* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
With triethylamine; trifluoroacetic anhydride In tetrahydrofuran at 0 - 20℃;
To an ice cold solution of 6-methoxy-pyridine-2-carboxylic acid amide (300 mg, 1.97 mmol) in THF (3 mL) were added triethylamine (1.25 mL, 8.68 mmol) and dropwise added TFAA (0.61 mL, 4.34 mmol). The reaction mixture was allowed to warm to room temperature and stirred overnight. The volatiles were concentrated in vacuo and the liquid residue was added dropwise to a vigorously stirred, ice cold, pH 7 phosphate buffer solution (5 mL). After 15 min of further stirring the yellowish solid was filtered and air dried for 1 h to yield 250 mg (95percent) of 6-methoxy-pyridine-2-carbonitrile as yellowish solid, mJz 135.4 [M + I]+.
[Referential Example 21]; 6-Methoxypyridine-2-carbonitrile; Copper(I) cyanide (2.68 g) was added to 2-bromo-6-methoxypyridine (5.62 g) in N,N-dimethylformamide (112 mL) at room temperature, followed by stirring at 165°C for 15 hours. The resultant mixture was cooled in air. Water and ethyl acetate was added to the mixture. The insoluble matter that was formed in the mixture was filtered by Celite. The filtrate was partitioned between water and ethyl acetate. The organic layer was dried over sodium sulfate anhydrate, followed by filtration. The solvent was evaporated under reduced pressure. The residue was subjected to silica gel column chromatography (hexane - ethyl acetate), to thereby give the title compound as a solid substance (1.78 g, 44percent) .1H-NMR(400MHz,CDCl3)δ: 3.96(3H,s), 6.95-6.98(1H,m), 7.29-7.31(1H,m), 7.64-7.67(1H,m). MS (EI)m/z: 134 (M+) .
Reference：
[1] Synlett, 2001, # 6, p. 765 - 768
[2] Journal of the Chemical Society. Perkin Transactions 1, 2002, vol. 2, # 1, p. 58 - 68
[3] Patent: EP1591443, 2005, A1, . Location in patent: Page/Page column 33
3
[ 17228-64-7 ]
[ 151-50-8 ]
[ 83621-01-6 ]
Reference：
[1] Chemistry - A European Journal, 2003, vol. 9, # 8, p. 1828 - 1836
Synthesis of 6-methoxypicolinonitrile:To a stirred solution of 2-bromo-6-methoxypyridine (5.0 g, 26.59 mmol) in DMF (50 mL) was added Cu(I)cyanide (7.14 g, 79.77 mmol) at room temperature. The resulting reaction mixture was heated at 100 °C and stirred for 16 h. The reaction mixture was diluted with water, filtered through a pad of celite and the filtrate was extracted with EtOAc. Combined organic layer was dried over sodium sulphate, filtered and concentrated in vacuo to obtain the crude product. The crude material was purified by silica gel column chromatography to afford 6-methoxypicolinonitrile (1.4 g, 39percent) as white solid. 1H-NMR (DMSO d6, 400 MHz): δ 7.94 (t, 1H), 7.64 (d, 1H), 7.18 (d, 1H), 3.92 (s, 3H); LC-MS: 99.14percent; 135.8 (M++l); (column; X-bridge C-18, (50x3.0 mm, 3.5μ); RT 3.31 min. 0.1percent Aq TFA: ACN; 0.8 ml/min); TLC: 10percent EtOAc/Hexane (Rf:
39%
at 100℃; for 16 h;
Synthesis of 6-methoxypicolinonitrile [0524] To a stirred solution of 2-bromo-6-methoxypyridine (5.0 g, 26.59 mmol) in DMF (50 mL) was added Cu(I)cyanide (7.14 g, 79.77 mmol) at room temperature. The resulting reaction mixture was heated at 100 °C and stirred for 16 h. The reaction mixture was diluted with water, filtered through a pad of celite and the filtrate was extracted with EtOAc. Combined organic layer was dried over sodium sulphate, filtered and concentrated in vacuo to obtain the crude product. The crude material was purified by silica gel column chromatography to afford 6-methoxypicolinonitrile (1.4 g, 39percent) as white solid. 1H-NMR (DMSO d6, 400 MHz): δ 7.94 (t, IH), 7.64 (d, IH), 7.18 (d, IH), 3.92 (s, 3H); LC-MS: 99.14percent; 135.8 (M++l); (column; X-bridge C-18, (50x3.0 mm, 3.5μ); RT 3.31 min. 0.1percent Aq TFA: ACN; 0.8 ml/min); TLC: 10percent EtOAc/Hexane (Rf: 0.3).
Reference：
[1] Journal of the Chemical Society. Perkin Transactions 1, 2002, vol. 2, # 1, p. 58 - 68
7
[ 626-05-1 ]
[ 83621-01-6 ]
Reference：
[1] Journal of the Chemical Society. Perkin Transactions 1, 2002, vol. 2, # 1, p. 58 - 68
[2] Synlett, 2001, # 6, p. 765 - 768
[3] Patent: EP1591443, 2005, A1,
8
[ 20773-98-2 ]
[ 7677-24-9 ]
[ 83621-01-6 ]
Reference：
[1] Chemical & Pharmaceutical Bulletin, 1985, vol. 33, # 2, p. 565 - 571
9
[ 100-70-9 ]
[ 67-56-1 ]
[ 586-98-1 ]
[ 83621-01-6 ]
Reference：
[1] Bulletin of the Chemical Society of Japan, 1982, vol. 55, # 9, p. 2906 - 2910
[2] Bulletin of the Chemical Society of Japan, 1982, vol. 55, # 9, p. 2906 - 2910
10
[ 100-70-9 ]
[ 64-17-5 ]
[ 586-98-1 ]
[ 83621-01-6 ]
Reference：
[1] Bulletin of the Chemical Society of Japan, 1982, vol. 55, # 9, p. 2906 - 2910
With triethylamine; trifluoroacetic anhydride; In tetrahydrofuran; at 0 - 20℃;
To an ice cold solution of <strong>[98276-69-8]6-methoxy-pyridine-2-carboxylic acid amide</strong> (300 mg, 1.97 mmol) in THF (3 mL) were added triethylamine (1.25 mL, 8.68 mmol) and dropwise added TFAA (0.61 mL, 4.34 mmol). The reaction mixture was allowed to warm to room temperature and stirred overnight. The volatiles were concentrated in vacuo and the liquid residue was added dropwise to a vigorously stirred, ice cold, pH 7 phosphate buffer solution (5 mL). After 15 min of further stirring the yellowish solid was filtered and air dried for 1 h to yield 250 mg (95%) of 6-methoxy-pyridine-2-carbonitrile as yellowish solid, mJz 135.4 [M + I]+.
Chemistry
Pharmaceutical Intermediates
Inhibitors/Agonists
Material Science
For Research Only
120K+ Compounds
Competitive Price
1-2 Day Shipping
