Tag: M.W:200-300

Reference of 189005-44-5 ,Some common heterocyclic compound, 189005-44-5, molecular formula is C17H16N2O2, 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.

One proceeds as described in Example 7 except that concentrated sulfuric acid is replaced by 5 ml of concentrated hydrochloric acid and the reaction mixture is refluxed for 5 hours. Thus 21.5 g of methyl-[6-methyl-2-(4-methyl-phenyl)-imidazo[1,2-a]pyridine-3-yl]-acetate are obtained. The product is identical in all respects with the compound prepared according to Example 1.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles. 189005-44-5, 6-Methyl-2-(4-methylphenyl)imidazol[1,2-a]pyridine-3-acetic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; EGIS GYOGYSZERGYAR RT.; EP1259509; (2005); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 1137475-57-0, 2-Bromo-4-chloro-5-nitropyridine, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound, Recommanded Product: 1137475-57-0, blongs to pyridine-derivatives compound. Recommanded Product: 1137475-57-0

A solution of 4-(aminomethyl)-1-boc-pipeiotadine (370 mg, 1.73 mmol) in acetonitrile (1 ml_) was added over 1 minute to a solution of 2-bromo-4-chloro-5-nitropyridine (373 mg, 1.57 mmol) and triethylamine (0.24 mL, 1.73 mmol) in acetonitrile (5 mL). The solution was stirred for 30 minutes then partitioned between dichloromethane and water. The aqueous phase was extracted with dichloromethane (x3) and the combined organic phases were dried (Na2SO4) and concentrated to give tert-butyl 4-((2-bromo-5-nitropyridin-4- ylamino)methyl)piperidine-1-carboxylate as a light brown foam (640 mg, 98%) which was used without further purification.1H NMR (MeOD, 400MHz) delta 8.82 (s, 1 H), 7.25 (s, 1 H), 4.14 (m, 3H), 3.35 (s, 1H), 1.97- 1.88 (m, 1H), 1.80 (m, 3H), 1.27-1.17 (m, 3H). LCMS (1) Rt = 2.35 min; m/z (ESI+) 415, 417 (MH+).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1137475-57-0, 2-Bromo-4-chloro-5-nitropyridine, and friends who are interested can also refer to it.

Reference:
Patent; CANCER RESEARCH TECHNOLOGY LIMITED; WO2009/44162; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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.754230-78-9, name is 3-(Benzyloxy)-5-bromopyridin-2-amine, molecular formula is C12H11BrN2O, molecular weight is 279.13, as common compound, the synthetic route is as follows.category: pyridine-derivatives

To a solution of 3-benzyloxy-5-bronio-pyridin-2-ylamine (278 mg, 1.00 mmol) in propionitrile (24 mL) and DMF (6 mL) were added iV-methyl-7^-(3-methyl-benzofuran-2- ylmethyl)acrylamide ( 252 mg, 1.10 mmol), (/-Pr)2EtN (0.35 mL, 2.00 mmol), Pd(OAc)2 (22 mg, 0.10 mmol) and P(o-tol)3 (61 mg, 0.20 mmol), and the mixture was de-oxygenated with argon for 15 min. The mixture was heated to reflux overnight, allowed to cool, filtered through a pad of diatomaceous earth, and the filtrate was concentrated. Purification by column chromatography (silica gel, CH2Cl2ZMeOH, 96:4) and then by slow precipitation fromCH?Cfe/hexanes gave the title compound (165 mg, 39%) as a pale yellow solid and as a mixture of amide rotamers: 1H NMR (300 MHz, DMSO-^5) delta 7.77 (s, IH), 7.58-6.94 (m, 12H), 6.27 (s, 2H), 5.19 (s, 2H), 5.00-4.78′ (ms 2H), 3.18-2.92 (m, 3H), 2.27 (s, 3H); MS (ESI) m/e 428 (M + H)+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,754230-78-9, 3-(Benzyloxy)-5-bromopyridin-2-amine, and friends who are interested can also refer to it.

Reference:
Patent; AFFINIUM PHARMACEUTICALS, INC.; WO2007/67416; (2007); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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.55876-84-1, name is Methyl 5-(bromomethyl)picolinate, molecular formula is C8H8BrNO2, molecular weight is 230.0586, as common compound, the synthetic route is as follows.Recommanded Product: Methyl 5-(bromomethyl)picolinate

INTERMEDIATE 38 – PREPARATION of methyl 5-(3-fluorobenzyl)picolinate. A mixture of 3-fluorophenylboronic acid (0.319 g; 2.28 mmol), methyl 5- (bromomethyl)picolinate (0.350 g; 0.230 mmol), tetrakis-(triphenylphosphine)-palladium(0) (0.175; 0.152 mmol) and N,N diisopropylethylamine (0.524 g; 3.04 mmol) in dimethoxyethane (9 mL) and water (3 mL) was irradiated in a microwave oven at 130°C for 20 minutes. The resulting solution was partitioned between water and ethyl acetate. The organic layer was separated and concentrated under reduced pressure. The crude residue was purified by flash chromatography on silica gel (eluent 1 to 10 percent ethyl acetate in dichlomethane) to afford 0.149 g (40percent) of the title compound as a yellow oil.ESI/APCI(+): 246 (M+H), 268(M+Na).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,55876-84-1, Methyl 5-(bromomethyl)picolinate, and friends who are interested can also refer to it.

Reference:
Patent; KATHOLIEKE UNIVERSITEIT LEUVEN, K.U. LEUVEN R&D; REMYND; GRIFFIOEN, Gerard; VAN DOOREN, Tom; ROJAS DE LA PARRA, Veronica; ALLASIA, Sara; MARCHAND, Arnaud; KILONDA, Amuri; CHALTIN, Patrick; WO2012/80221; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 67443-38-3, 5-Bromo-2-chloro-3-nitropyridine, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound, category: pyridine-derivatives, blongs to pyridine-derivatives compound. category: pyridine-derivatives

Method I: 5-bromo-2-chloro-3-nitropyridine (100 mg, 0.42 mmol) and Ethyl glycolate (0.044 mL, 0.46 mmol) were dissolved in THF (5 mL) and cooled to 0C. Sodium hydride (0.015 mL, 0.46 mmol) was added and the mixture was stirred for 1hr at room temperature. Reaction mixture was poured in ice water and extracted with EtOAc (2 x 10ml). The organiclayer was washed with brine (10ml), dried over sodium sulphate and concentrated. The crude product was purified by flash column using 100-200 silica gel to ethyl 2-(5-bromo-3-nitropyridin-2-yloxy)acetate (105 mg, 82 %) 9(b). 1H NMR (300 MHz, DMSO-d6) delta = 1.27 (s, 3H), 4.25 (q, 2 H), 5.12 (s, 2H) 8.40 (d, J = 2.07 Hz, 1 H), 8.47 (d, J = 2.07 Hz, 1 H); ESMS: m/z 306.8 [M+1]

The synthetic route of 67443-38-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Hameed P., Shahul; Shanbhag, Gajanan; Shinde, Vikas; Chinnapattu, Murugan; Manjrekar, Praveena; Puttur, Jayashree; Patil, Vikas; Ugarkar, Bheemarao; Synthetic Communications; vol. 43; 24; (2013); p. 3315 – 3321;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 911434-05-4 , The common heterocyclic compound, 911434-05-4, name is 5-Bromo-2-methyl-3-nitropyridine, molecular formula is C6H5BrN2O2, 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.

To a solution of 5- bromo-2-methyl-3-nitropyridine (1) (15 g, 69.4 mmol) in EtOH (300 mL) and water (70 ml), was added iron powder (46.7 g, 833 mmol) and ammonium chloride (4.5 g, 83.4 mmol) successively at rt. The reaction mixture was heated to 90 C for 40 min. The reaction was filtered hot and rinsed with EtOAc. The filtrate was washed with a saturated aqueous solution of sodium bicarbonate (200 mL), brine, dried over magnesium sulfate and solvent removed in vacuo to give the title compound as an orange solid, (11.7 g, 62.9 mmol, 90%). LCMS (ESI) calc’d for C6H7BrN2 [M+H]+: 187, found: 187, 188.

The synthetic route of 911434-05-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP & DOHME CORP.; BARR, Kenneth Jay; BEINSTOCK, Corey; MACLEAN, John; ZHANG, Hongjun; BERESIS, Richard Thomas; ZHANG, Dongshan; WO2014/26327; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 152684-30-5, In the chemical reaction process,reaction time,type of solvent,can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product.An updated downstream synthesis route of 152684-30-5 as follows.

To a suspension of 5-bromo-2-methoxy-3-nitropyridine (0.4 g, 1.72 mmol) in EtOH(5 mL) and H20 (5 mL) was added iron powder (0.38 g, 6.87 mmol) and NH4Cl (0.39 g, 7.21mmol). The reaction refluxed for 1 h, then cooled down to rt and concentrated in vacuo. Theresidue was diluted with EtOAc (1 0 mL) and the resulted mixture was filtered through a pad ofcelite. The filtrate was extracted with EtOAc (10 mL x 3) and the combined organic phases werewashed with brine (10 mL), dried over anhydrous Na2S04 and concentrated in vacuo to give thetitle compound as a yellow solid (0.3 g, 86%). The title compound was characterized byLC-MS and 1H NMR as shown below:LC-MS (ESI, pos. ion) m/z: 203 [M+Ht;1H NMR (400 MHz, CDCh) 8 (ppm): 3.92 (s, 3H), 4.86 (s, 2H), 7.03 (d, J = 2.0 Hz, 1H), 7.41 (d,J = 2.0 Hz, 1H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,152684-30-5, its application will become more common.

Reference:
Patent; CALITOR SCIENCES, LLC; SUNSHINE LAKE PHARMA CO., LTD.; XI, Ning; LI, Zhuo; WANG, Tingjin; WU, Zuping; WEN, Qiuling; WO2014/22128; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 78686-79-0, Adding some certain compound to certain chemical reactions, such as: 78686-79-0, name is Methyl 5-bromo-2-chloronicotinate,molecular formula is C7H5BrClNO2, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 78686-79-0.

INTERMEDIATE 31Methyl 2-chloro-5-methylnicotinate; To a solution of methyl 5-bromo-2-chloronicotinate (1.05g, 4.19mmol), K3PO4 (2.95g, 13.90mmol), methylboronic acid (0.32g, 5.26mmol) and tricyclohexylphosphine (0.11g, 0.39mmol) in toluene/water (16ml/0.8ml) under nitrogen atmosphere was added Pd(OAc)2 (0.04g, 0.18mmol). The mixture was heated at 1000C overnight under nitrogen atmosphere. The reaction mixture was then cooled to room temperature and concentrated in vacuum. Ethyl acetate was added to the residue and this organic layer was washed with water, brine, dried over MgSO4, filtered and the solvent evaporated under vacuum to yield the desired product as a yellow oil. Yield=87% LRMS: m/z 186 (M+1 )+ Retention time: 4.84min

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles. 78686-79-0, Methyl 5-bromo-2-chloronicotinate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; LABORATORIOS ALMIRALL, S.A.; WO2008/77639; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 65973-52-6, 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 65973-52-6, name is Methyl 4,6-dichloronicotinate. This compound has unique chemical properties. The synthetic route is as follows.

[00217] Step B; 4.6-Dichloronicotinic acid:[00218] To a solution of methyl 4,6-dichloronicotinate in a mixture of THF (400 ml), MeOH ( 100 ml) andH2O ( 100 ml) was added a solution of NaOH (10 g) in 40 ml H2O. The mixture was stirred for 40 min. at room temp. Then, the solvents were reduced and it was acidified with cone. HCl to a pH of about 2. It was extracted using a mixture of Et2O/EtOAc and the organic layer was dried with Na2SO4. The solvents were removed and the residue dried in vacuo to obtain the title compound as a white solid (12.3 g, 69%). Rf (CHCl3/MeOH 10:1) = 0.85. 1H-NMR (300 MHz, DMSO-D6): delta = 8.80 (s, 1H), 7.90 (s, 1H).

While traditionally a conservative industry, chemical producers will need to modernize their PR strategies to stay relevant.we look forward to future research findings about 65973-52-6, Methyl 4,6-dichloronicotinate.

Reference:
Patent; ARDEA BIOSCIENCES, INC.; WO2008/89459; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 94446-97-6, 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. 94446-97-6, name is 2-Bromo-3-(bromomethyl)pyridine. A new synthetic method of this compound is introduced below.

This intermediate was generated by a modified procedure based on that disclosed in Viswanathan, R., et al., J. Am.Chem. Soc., 125, 163 (2003) and Synthesis 2, 330 (2005). A three neck round bottom flask with a stir bar was chargedwith I-5 (40.1 g, 135.7 mmol), I-7 (8.2 g, 13.6 mmol), powdered KOH (69.1 g, 1221.4 mmol), and DCM (600 ml).The opaque yellow suspension was cooled to -78C and the flask fitted with a dropping funnel. A suspension of I-4 (152.0 g, 610.7 mmol) in 400 ml DCM was transferred to the dropping funnel and added to the reaction at -78C over about 1 hr. The suspension in the dropping funnel would occasionally settle and the solid would be resuspended. After the end of the addition the funnel was rinsed with an additional 200 ml of DCM and the rinse was added to the reaction. After 10 hrs at -78C. the reaction was allowed to stir overnight as it warmed to room temperature. Analysis of the reaction by HPLC and TLC showed complete conversion of I-4. The reaction was diluted with 3 L of DCM transferred to a 15 L reactor and extracted 2 x 1 L of water. During the separation the organic phase appeared cloudy due to a solid formed from I-4. The organic phase was collected then washed with NaCl (satd.aqueous), dried over anhydrous sodium sulphate, filtered and concentrated to near dryness and purified by normal phase flash chromatography. A three solvent mobile phase was used for the separation; initially DCM/hexanes to elute the excess I-4, followed by EtOAc/Hexanes to elute the title compound (S)-tert-butyl 3-(2-bromopyridin-3-yl)-2-((diphenylmethylene)amino)propanoate (I-8) obtained as a yellow solid (23.1 g, 226.0 mmol, 37%). H1 NMR (400 MHz, CDCl3) delta 8.20(1H, dd, J=4.2 Hz), 7.60(2H, d, J=8 Hz), 7.56(1H, dd,J=4.2 Hz), 7.45-7.25(6H, m), 7.12(1H, dd, J=8.4 Hz), 6.67(1H, d, J=d Hz), 4.39(1H, dd, J=8.4 Hz), 3.39(1H, dd,J=12.4 Hz), 3.21(1H, dd, J=12.4 Hz), 1.46(9H, s), MS(LC/MS) m/z observed 464.87, expected 465.12 [M+H].

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,94446-97-6, its application will become more common.

Reference:
Patent; viDA Therapeutics Inc.; Cameron, Dale R.; (36 pag.)US9458192; (2016); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem