Pyridine-derivatives

Electric Literature of 14432-12-3, With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.14432-12-3, name is 4-Amino-2-chloropyridine, molecular formula is C5H5ClN2, molecular weight is 128.56, as common compound, the synthetic route is as follows.

A solution of 4-amino-2-chloropyridine (1.28 gm, 10 mmol) and di-tert-butyl dicarbonate (2.21 gm, 10.1 mmol) in THF (20 mL) was cooled to 00C and a solution of IM lithium bis(trimethylsilyl)amide in THF ( 20 mL, 20 mmol) was added slowly maintaining the temperature below 00C. The reaction was allowed to warm to room temperature over one hour and then quenched by the addition of 1.5 N aqueous ammonium chloride (15 mL). After stirring for several hours the reaction was extracted into ethyl acetate, washed with brine, the organic layer dried (Na2SO4), filtered and evaporated. The residue was triturated with diethyl ether give pure tert-butyl (2-chloropyridin-4- yl)carbamate. The mother liquors were chromatographed on silica gel eluting with 25 – 45% ethyl acetate/ hexane to afford more product. EPO A solution of tert-butyl (2-chloropyridin-4-yl)carbamate (1.14 gm, 5 mmol) in dry THF (20 mL) was cooled to -700C under an inert atmosphere and 1.7 M t-butyl lithium/pentane (8 mL, 13.5 mmol) was slowly added. The reaction was stirred for two hours and then dry DMF (1.2 mL, 15.5 mmol) was added. The reaction was allowed to slowly warm to room temperature over a three hour period. The reaction mixture was quenched with 3 N HCl (12 mL) and diluted with diethyl ether. The ether layer was washed with aqueous NaHCtheta3, dried (over Na2SO4), filtered and evaporated. The residue was triturated with cold diethyl ether to give pure t-butyl (2-chloro-3-formylrhoyridin-4- yl)carbamate. The mother liquors were chromatographed on silica gel eluting with 15-20% ethyl acetate/hexane to give additional product. 1H-NMR(5OO MHz, CDCI3): deltall.O (IH, br s), 10.52 (IH, s), 8.38 (IH, d, J= 6 Hz), 8.31 (IH, d, J= 6 Hz), 1.54 (9H, s); m/e (m+1): 257.2.

The chemical industry reduces the impact on the environment during synthesis 14432-12-3, I believe this compound will play a more active role in future production and life.

Reference:
Patent; MERCK & CO., INC.; WO2006/135627; (2006); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 73870-24-3 ,Some common heterocyclic compound, 73870-24-3, molecular formula is C6H7Br2N, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route.

Cytosine-pyridine (2) was obtained by mixing cytosine (0.65 g,5.93 mmol, 3 eq) and KI (10 mg, catalytic amount) in 10 mL of dry DMF. After degassing the suspension with argon for 15 min, NaH(0.118 g, 4.9 mmol, 2.5 eq) was added and the mixture was stirredfor 30 min. A solution of 4-(bromomethyl)pyridine hydrobromide(0.5 g, 1.97 mmol, 1 eq) in 4 mL of dry DMF was slowly added to themixture. The mixture was stirred at 40C overnight and the reac-tion progress was followed by TLC. The crude was dried undervacuum and then washed with a minimum amount of water. Theproduct was puried by column chromatography (silica gel, MeOH:Et3N: DCM 1:0.2:20) affording compound 2 (120 mg, 30%) as awhite powder; dH (500 MHz, DMSO-d6) 4.87 (2H, s, Ha), 5.73 (1H, d,3J 7.2 Hz, Hb), 7.08 (1H, s, brd, NH), 7.17 (2H, d,3J 6.0 Hz, Hm),7.21 (1H, s, brd, NH), 7.69 (1H, d,3J 7.2 Hz, Hc), 8.50 (2H, d,3J 6.0 Hz, Ho); dC (126 MHz, DMSO-d6) 50.6 (Ca), 93.9 (Cb), 122.0(Cm), 146.1 (Cc), 147.0 (Cp), 149.7 (Co), 155.7 (Cd), 166.1 (Ce); HRMS(ESI): MH, found 203.0934. C10H10N4O requires 203.0927; IR(cm1): 3337.24, 3115.39, 1652.03, 1597.71, 1486.09, 1423.17,1384.39, 1369.72, 1278.91, 1208.06, 1130.29, 965.29, 815.97, 781.56,704.43, 682.80, 567.57, 521.43, 474.65, 405.44.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,73870-24-3, its application will become more common.

Reference:
Article; Bulach, Veronique; Hosseini, Mir Wais; Jouaiti, Abdelaziz; Kyritsakas, Nathalie; Tufenkjian, Elsa; Tetrahedron; vol. 76; 9; (2020);,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 13534-98-0, Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps,and cheap raw materials. 13534-98-0, name is 4-Amino-3-bromopyridine. A new synthetic method of this compound is introduced below.

General procedure: A mixture of amino pyridine 1 (1.0 mmol), 10%Pd/C (0.010 mmol), CuI (0.010 mmol), PPh3 (0.022 mmol) and Cs2CO3 (3 mmol) in PEG-400 (3 mL) was stirred for 15 min at room temperature under a nitrogen atmosphere. To this was added an appropriate iodoarene 2 (1.0 mmol) and the mixture was stirred further for 10 min. The mixture was then stirred at 95 – 100 C for 2.5 h under ultrasound irradiation using a laboratory ultrasonic bath Sonorex Super RK 510H model producing irradiation of 35 kHz. After cooling the mixture to room temperature an appropriate terminal alkyne 3 (1.2 mmol) was added to it. The mixture was then stirred again at 95-100 C for 4h under ultrasound irradiation. After completion of the reaction (indicated by TLC), the mixture was diluted with cold water (30 mL) and extracted with CH2Cl2 (3 x 10 mL). The organic layers were collected, combined, washed with cold water (2 x 15 mL), dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The crude product was then purified by column chromatography on silica gel using EtOAc / n-hexane as a solvent system.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,13534-98-0, 4-Amino-3-bromopyridine, and friends who are interested can also refer to it.

Reference:
Article; Dandela, Rambabu; Nath Singh, Shambhu; Pal, Manojit; Ramamohan, Hindupur; Siddaiah, Vidavalur; Venkateshwarlu, Rapolu; Tetrahedron Letters; (2019);,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 5470-17-7, With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.5470-17-7, name is 3-Bromo-2-chloro-5-nitropyridine, molecular formula is C5H2BrClN2O2, molecular weight is 237.44, as common compound, the synthetic route is as follows.

Step 1: 3-bromo-2-(2-methoxyethoxy)-5-nitropyridine (Intermediate 15)To a stirred solution of S-bromo-l-chloro-S-nitropyridine (1.5 g, 6.32 mmol) and 2- methoxyethanol (0.961 g, 12.63 mmol) in DMF (10 mL) , potassium carbonate (1.746 g, 12.63 mmol) was added portion wise and the mixture was stirred at 60 0C for 5 hr. Reaction mixture was then cooled to RT, diluted with ethyl acetate (150ml), washed successively with water and then brine, organic layer was collected, dried over sodium sulfate and concentrated to give crude 3-bromo-2-(2-methoxyethoxy)-5-nitropyridine (1.500 g, 86 %) as brown solid. MS (ES+): 277.9 for C8H9BrN2O4

The chemical industry reduces the impact on the environment during synthesis 5470-17-7, I believe this compound will play a more active role in future production and life.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2009/147431; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 7598-35-8, The major producers of chemicals have been the Europe, Japan and China. Due to the growing call for a cleaner, greener environment, people will have to find innovative ways to maintain their relevance. Here is a compound 7598-35-8, name is 2-Bromopyridin-4-amine. This compound has unique chemical properties. The synthetic route is as follows.

Et3N (0.64 ml_) and di-tert-butyl dicarbonate (4.62 mmol) at 0 C were added to a solution of commercially available 4-amino-2-bromopyirdine (2.31 mmol, 400 mg) in anhydrous THF (5.9 ml_), and the reaction mixture was stirred overnight at room temperature. The solvent was removed under reduced pressure; then the residue was diluted with EtOAc and sequentially washed with a saturated solution of sodium bicarbonate, water and brine. The organic phase was dried with Na2S04 and concentrated. The crude reaction product was purified by column chromatography over silica gel with a mixture of n- hexane/EtOAc 8:2 as the eluent to afford intermediate O (72% yield). [1H-NMR (CDCIs) d (ppm): 1.52 (s, 9H), 6.68 (bs, 1 H), 7.18 (dd, 1 H, J = 5.6, 2.0 Hz), 7.64 (d, 1 H, J = 1.9 Hz), 8.17 (d, 1 H, J = 5.7 Hz).]

According to the analysis of related databases, 7598-35-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; UNIVERSITA’ DI PISA; CALDERONE, Vincenzo; MINUTOLO, Filippo; TUCCINARDI, Tiziano; TESTAI, Lara; GRANCHI, Carlotta; MARTELLI, Alma; CITI, Valentina; DE LORENZO GARDINAL, Virginia; LENZI, Giulia; LEO, Francesca; MALLOGGI, Giulia; (0 pag.)WO2019/162911; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 14432-12-3 ,Some common heterocyclic compound, 14432-12-3, molecular formula is C5H5ClN2, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route.

Preparation 13 : 2-Chloro-5-iodop; Silver sulfate (7.1g, 22.8mmol) and 4-amino-2-chloropyridine (4.06g, 31.6mmol) were added to a solution of iodine (5.65g, 22.3mmol) in ethanol (10OmL) and the reaction mixture stirred at rt for 72h. The bright yellow suspension was filtered, washed with methanol and the filtrate concentrated in vacuo. The residue was partitioned between saturated Na2CO3 solution (20OmL) and EtOAc (200ml). After separation the organic layer was washed with Na2S2O3 solution (5OmL, 25%) and brine (5OmL), dried (MgSO4), concentrated in vacuo and purified by chromatography on silica gel eluting with iso- EPO hexane/EtOAc (3:1 to 2.5:1) to give the title compound, delta? (CDCl3): 4.81 (2H, br s), 6.63 (IH, s), 8.38 (IH, s); m/z (ES+) = 254.86 [M+ H]+; RT = 2.51min.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,14432-12-3, its application will become more common.

Reference:
Patent; PROSIDION LIMITED; WO2006/59164; (2006); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 116632-24-7, Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps,and cheap raw materials. 116632-24-7, name is 2-Amino-4,6-dichloropyridine. A new synthetic method of this compound is introduced below.

Reference Example 7 4-chloro-6-phenoxypyridin-2-amine (0379) 630 mg (6.69 mmol) of phenol and 1.00 g (6.13 mmol) of 4,6-dichloropyridin-2-amine were added at room temperature to a mixed solution of 250 mg (6.56 mmol) of 63 wt. % sodium hydride (dispersion in mineral oil) and 15 ml dimethyl sulfoxide. After completion of the addition, said reaction mixture liquid was stirred for 14 hours at 100 C. After completion of the stirring, the reaction was stopped by addition of 30 ml of water, and said reaction liquid was extracted with diethyl ether (2×30 ml). The organic layer obtained was dried with anhydrous sodium sulfate, and the solvent distilled off under reduced pressure. The residue obtained was purified by silica gel chromatography (n-hexane:ethyl acetate=9:1 to 1:9), and 70 mg of the desired compound were obtained as a brown solid. (0380) 1H-NMR (CDCl3, Me4Si, 300 MHz): delta 7.44-7.35 (m, 2H), 7.21-7.18 (m, 1H), 7.13-7.09 (m, 2H), 6.19 (s, 1H), 6.08 (s, 1H), 4.52 (brs, 2H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,116632-24-7, 2-Amino-4,6-dichloropyridine, and friends who are interested can also refer to it.

Reference:
Patent; SYNGENTA PARTICIPATIONS AG; NAKAYA, Yoshihiko; MASUZAWA, Yoshihide; FURUHASHI, Takamasa; MIYAKADO, Yuuki; HOTTA, Hiroyasu; INABA, Masamitsu; (76 pag.)US2016/221998; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 74115-12-1, With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.74115-12-1, name is 5-Chloro-3-hydroxypyridine, molecular formula is C5H4ClNO, molecular weight is 129.5444, as common compound, the synthetic route is as follows.

With ice cooling, 30 g of 5-chloropyridin-3-ol (232 mmol, 1 equivalent) were dissolved in 228 ml of concentrated sulfuric acid, and 24 ml of concentrated nitric acid were added slowly at 0 C. The reaction was warmed to RT and stirred overnight. The mixture was stirred into an ice/water mixture and stirred for 30 min. The solid was filtered off, washed with cold water and air-dried. This gave 33 g (82% of theory) of the title compound which was used without further purification for the next reaction. LC-MS (Method 1): Rt=0.60 min MS (ESneg): m/z=172.9/174.9 (M-H)- 1H-NMR (400 Mhz, DMSO-d6): delta=7.71 (d, 1H); 8.10 (d, 1H); 12.14 (br. 1H).

The chemical industry reduces the impact on the environment during synthesis 74115-12-1, I believe this compound will play a more active role in future production and life.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; VAKALOPOULOS, Alexandros; BROCKSCHNIEDER, Damian; WUNDER, Frank; STASCH, Johannes-Peter; MARQUARDT, Tobias; DIETZ, Lisa; LI, Volkhart Min-Jian; (50 pag.)US2017/304278; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 1196154-43-4, With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.1196154-43-4, name is Ethyl 2-chloro-6-(trifluoromethyl)isonicotinate, molecular formula is C9H7ClF3NO2, molecular weight is 253.6056, as common compound, the synthetic route is as follows.

Step 3: 2-[2-chloro-6-(trifluoromethyl)pyridin-4-yl]propan-2-ol Ethyl 2-chloro-6-(trifluoromethyl)isonicotinate (0.35 g, 1.4 mmol) was dissolved in tetrahydrofuran (13.8 mL) and was cooled to -78 C., then 3.0 M methylmagnesium bromide in ether (1.4 mL, 4.1 mmol) was added. The reaction was stirred at -78 C. for 3 hours at which time LCMS analysis showed absence of starting material. The reaction was quenched with saturated NH4Cl and was partitioned between water/1 N HCl and EtOAc, the phases were separated and the aqueous phase was washed with additional EtOAc. The combined organic phase was washed with water, saturated NaCl, dried over MgSO4, filtered and evaporated to dryness to provide the crude product. NMR analysis showed that it consisted of a ?1:1 mixture of the alcohol and the methyl ketone intermediate. The crude material used in the next reaction without purification. NMR 400 MHz NMR(CDCl3): delta 7.70 (s, 1H), 7.63 (s, 1H), 1.60 (s, 6H)

Statistics shows that 1196154-43-4 is playing an increasingly important role. we look forward to future research findings about Ethyl 2-chloro-6-(trifluoromethyl)isonicotinate.

Reference:
Patent; Incyte Corporation; Vaddi, Krishna; US2015/246046; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

The major producers of chemicals have been the Europe, Japan and China. Due to the growing call for a cleaner, greener environment, people will have to find innovative ways to maintain their relevance. Here is a compound 865156-50-9, name is (4-Bromopyridin-2-yl)methanamine. This compound has unique chemical properties. The synthetic route is as follows. Product Details of 865156-50-9

Compound 39.2. N-((4-Bromopyridin-2-yl)methyl)formamide. To a 500-mL round-bottom flask, was placed (4-bromopyridin-2-yl)methanamine (compound 39.1, 8.0 g, crude) and formic acid (200 mL). The solution was stirred for 2 h at 100 C, then cooled and the pH was adjusted to 7 by careful and slow addition of aqueous sodium carbonate (sat.). The aqueous phase was extracted with ethyl acetate (3 x 200 mL) and the combined organic layers were washed with brine (3 x 30 mL), dried (Na2S04), filtered, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography with ethyl acetate as the eluent to yield the title compound as a yellow oil (8.0 g, 90% pure, 65% yield over 2 steps).

With the rapid development of chemical substances, we look forward to future research findings about 865156-50-9.

Reference:
Patent; 3-V BIOSCIENCES, INC.; OSLOB, Johan D.; MCDOWELL, Robert S.; JOHNSON, Russell; YANG, Hanbiao; EVANCHIK, Marc; ZAHARIA, Cristiana A.; CAI, Haiying; HU, Lily W.; WO2014/8197; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem