Category: 718608-10-7

As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 718608-10-7, name is 5-(Bromomethyl)-2-methylpyridine hydrobromide, molecular formula is C7H9Br2N, The compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below. SDS of cas: 718608-10-7

Sodium hydride (800mg, 60% dispersion in mineral oil, 20MMOL) and imidazole (54mg, 0. 8MMOL) were added portionwise to a cooled (-15C) solution of the acid from preparation 37 (960mg, 4MMOL) in tetrahydrofuran (40ML) and the solution stirred for 1 hour. A suspension of the bromide from preparation 40 (1.28g, 4. 8MMOL) and N-methyl morpholine (535mg, 5. 3MMOL) in TETRAHYDROFURAN (10M .) was added so as to maintain the temperature BELOW-1 5C, and the reaction then stirred for a further 2 hours. The reaction was allowed to warm to room temperature and stirred for a further 18 hours. The mixture was then basified to pH 11, washed with ethyl acetate, carefully acidifed to pH 5 and extracted with ethyl acetate. These combined organic solutions were washed with brine, dried (MGS04) and evaporated under reduced pressure. The crude product was purified by column chromatography on silica gel using DICHLOROMETHANE : methanol (94: 6) as eluant, and the product triturated with ether to afford the title compound, 177mg ;’H NMR (CDC13, 400MHZ) 8 : 1.42 (s, 9H), 2.62-2. 80 (m, 5H), 3.64 (m, 2H), 4.18 (m, 1 H), 4.60 (s, 2H), 5.50 (d, 1 H), 7.40 (d, 1 H), 7.83 (d, 1 H), 8.62 (s, 1 H) ; LRMS: M/Z (ES-) 323 [M-H]-.

With the rapid development of chemical substances, we look forward to future research findings about 718608-10-7.

Reference:
Patent; PFIZER LIMITED; PFIZER INC.; WO2004/56750; (2004); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 718608-10-7, name is 5-(Bromomethyl)-2-methylpyridine hydrobromide, molecular formula is C7H9Br2N, The compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below. SDS of cas: 718608-10-7

Sodium hydride (800mg, 60% dispersion in mineral oil, 20MMOL) and imidazole (54mg, 0. 8MMOL) were added portionwise to a cooled (-15C) solution of the acid from preparation 37 (960mg, 4MMOL) in tetrahydrofuran (40ML) and the solution stirred for 1 hour. A suspension of the bromide from preparation 40 (1.28g, 4. 8MMOL) and N-methyl morpholine (535mg, 5. 3MMOL) in TETRAHYDROFURAN (10M .) was added so as to maintain the temperature BELOW-1 5C, and the reaction then stirred for a further 2 hours. The reaction was allowed to warm to room temperature and stirred for a further 18 hours. The mixture was then basified to pH 11, washed with ethyl acetate, carefully acidifed to pH 5 and extracted with ethyl acetate. These combined organic solutions were washed with brine, dried (MGS04) and evaporated under reduced pressure. The crude product was purified by column chromatography on silica gel using DICHLOROMETHANE : methanol (94: 6) as eluant, and the product triturated with ether to afford the title compound, 177mg ;’H NMR (CDC13, 400MHZ) 8 : 1.42 (s, 9H), 2.62-2. 80 (m, 5H), 3.64 (m, 2H), 4.18 (m, 1 H), 4.60 (s, 2H), 5.50 (d, 1 H), 7.40 (d, 1 H), 7.83 (d, 1 H), 8.62 (s, 1 H) ; LRMS: M/Z (ES-) 323 [M-H]-.

With the rapid development of chemical substances, we look forward to future research findings about 718608-10-7.

Reference:
Patent; PFIZER LIMITED; PFIZER INC.; WO2004/56750; (2004); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 718608-10-7 , The common heterocyclic compound, 718608-10-7, name is 5-(Bromomethyl)-2-methylpyridine hydrobromide, molecular formula is C7H9Br2N, 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.

A mixture of 8-chloro-3-((1S,2S)-2-hydroxycyclohexyl)-6-(4,4,5,5-tetramethyl- 1,3,2-dioxaborolan-2-yl)quinazolin-4(3H)-one (130 mg, 0.321 mmol), cesium carbonate (314 mg, 0.964 mmol) and 5-(bromomethyl)-2-methylpyridine hydrobromide (103 mg, 0.385 mmol) in THF (5.0 ml) was sparged under nitrogen for 5 minutes. The mixture was treated with [1,1?- bis(diphenylphosphino)ferrocene]dichloropalladium(II), complex with dichloromethane (26.2 mg, 0.032 mmol), sparged under nitrogen (3 minutes) and then heated at 60 C for 2 hours. The mixture was cooled to room temperature, diluted with ethyl acetate (25 mL) and water (25 mL), and extracted with ethyl acetate (3 x 25 mL). The combined organic extracts were washed with brine, dried with sodium sulfate, filtered, and concentrated in vacuo. The residue was purified by preparative reverse phase HPLC (90:10 to 0:100; water containing 0.1% formic acid : acetonitrile containing 0.1% formic acid) to yield the title compound. 1H NMR (400MHz, CD3OD): delta 8.35 (d, J = 2.0 Hz, 2H), 8.02 (d, J = 1.6 Hz, 1H), 7.80 (d, J = 2.0 Hz, 1H), 7.62 (d, J = 8.0, 2.0 Hz, 1H), 7.27 (d, J = 8.0 Hz, 1H), 4.51- 4.49 (m, 1H), 4.13 (s, 2H), 4.07- 4.02 (m, 1H), 2.51 (s, 3H), 2.20- 2.10 (m, 1H), 1.97- 1.84 (m, 4H), 1.48- 1.46 (m, 3H) ppm. LRMS C21H23ClN3O2: calc?d 384.1, obs 384.2 (M+H) +.

The synthetic route of 718608-10-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP & DOHME CORP.; BESHORE, Douglas C.; MOHANTY, Subhendu Kumar; LATTHE, Prashant R.; KUDUK, Scott D.; HOYT, Scott B.; (107 pag.)WO2017/155816; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 718608-10-7 , The common heterocyclic compound, 718608-10-7, name is 5-(Bromomethyl)-2-methylpyridine hydrobromide, molecular formula is C7H9Br2N, 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.

A mixture of 8-chloro-3-((1S,2S)-2-hydroxycyclohexyl)-6-(4,4,5,5-tetramethyl- 1,3,2-dioxaborolan-2-yl)quinazolin-4(3H)-one (130 mg, 0.321 mmol), cesium carbonate (314 mg, 0.964 mmol) and 5-(bromomethyl)-2-methylpyridine hydrobromide (103 mg, 0.385 mmol) in THF (5.0 ml) was sparged under nitrogen for 5 minutes. The mixture was treated with [1,1?- bis(diphenylphosphino)ferrocene]dichloropalladium(II), complex with dichloromethane (26.2 mg, 0.032 mmol), sparged under nitrogen (3 minutes) and then heated at 60 C for 2 hours. The mixture was cooled to room temperature, diluted with ethyl acetate (25 mL) and water (25 mL), and extracted with ethyl acetate (3 x 25 mL). The combined organic extracts were washed with brine, dried with sodium sulfate, filtered, and concentrated in vacuo. The residue was purified by preparative reverse phase HPLC (90:10 to 0:100; water containing 0.1% formic acid : acetonitrile containing 0.1% formic acid) to yield the title compound. 1H NMR (400MHz, CD3OD): delta 8.35 (d, J = 2.0 Hz, 2H), 8.02 (d, J = 1.6 Hz, 1H), 7.80 (d, J = 2.0 Hz, 1H), 7.62 (d, J = 8.0, 2.0 Hz, 1H), 7.27 (d, J = 8.0 Hz, 1H), 4.51- 4.49 (m, 1H), 4.13 (s, 2H), 4.07- 4.02 (m, 1H), 2.51 (s, 3H), 2.20- 2.10 (m, 1H), 1.97- 1.84 (m, 4H), 1.48- 1.46 (m, 3H) ppm. LRMS C21H23ClN3O2: calc?d 384.1, obs 384.2 (M+H) +.

The synthetic route of 718608-10-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP & DOHME CORP.; BESHORE, Douglas C.; MOHANTY, Subhendu Kumar; LATTHE, Prashant R.; KUDUK, Scott D.; HOYT, Scott B.; (107 pag.)WO2017/155816; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 718608-10-7 , The common heterocyclic compound, 718608-10-7, name is 5-(Bromomethyl)-2-methylpyridine hydrobromide, molecular formula is C7H9Br2N, 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.

A mixture of 8-chloro-3-((1S,2S)-2-hydroxycyclohexyl)-6-(4,4,5,5-tetramethyl- 1,3,2-dioxaborolan-2-yl)quinazolin-4(3H)-one (130 mg, 0.321 mmol), cesium carbonate (314 mg, 0.964 mmol) and 5-(bromomethyl)-2-methylpyridine hydrobromide (103 mg, 0.385 mmol) in THF (5.0 ml) was sparged under nitrogen for 5 minutes. The mixture was treated with [1,1?- bis(diphenylphosphino)ferrocene]dichloropalladium(II), complex with dichloromethane (26.2 mg, 0.032 mmol), sparged under nitrogen (3 minutes) and then heated at 60 C for 2 hours. The mixture was cooled to room temperature, diluted with ethyl acetate (25 mL) and water (25 mL), and extracted with ethyl acetate (3 x 25 mL). The combined organic extracts were washed with brine, dried with sodium sulfate, filtered, and concentrated in vacuo. The residue was purified by preparative reverse phase HPLC (90:10 to 0:100; water containing 0.1% formic acid : acetonitrile containing 0.1% formic acid) to yield the title compound. 1H NMR (400MHz, CD3OD): delta 8.35 (d, J = 2.0 Hz, 2H), 8.02 (d, J = 1.6 Hz, 1H), 7.80 (d, J = 2.0 Hz, 1H), 7.62 (d, J = 8.0, 2.0 Hz, 1H), 7.27 (d, J = 8.0 Hz, 1H), 4.51- 4.49 (m, 1H), 4.13 (s, 2H), 4.07- 4.02 (m, 1H), 2.51 (s, 3H), 2.20- 2.10 (m, 1H), 1.97- 1.84 (m, 4H), 1.48- 1.46 (m, 3H) ppm. LRMS C21H23ClN3O2: calc?d 384.1, obs 384.2 (M+H) +.

The synthetic route of 718608-10-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP & DOHME CORP.; BESHORE, Douglas C.; MOHANTY, Subhendu Kumar; LATTHE, Prashant R.; KUDUK, Scott D.; HOYT, Scott B.; (107 pag.)WO2017/155816; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem