Methyl iodide → 2-Methylsulfanylthieno[2,3-b]pyridine-3-carboxylic Acid Ethyl Ester

HRID 1911092

反応式

HRID 1911092 の反応式
Cl[C:2]1[C:7]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:6][CH:5]=[CH:4][N:3]=1.[C:14](=[S:16])=[S:15].[H-].[Na+].[CH3:19]I>CS(C)=O>[CH2:12]([O:11][C:9]([C:8]1[C:7]2[C:2](=[N:3][CH:4]=[CH:5][CH:6]=2)[S:15][C:14]=1[S:16][CH3:19])=[O:10])[CH3:13]

参加物

6

反応物 4

HCID 6328Methyl iodideHCID 6348Carbon DisulfideHCID 24758Sodium hydrideHCID 15326671Ethyl 2-(2-chloropyridin-3-yl)acetate

生成物 1

HCID 153266732-Methylsulfanylthieno[2,3-b]pyridine-3-carboxylic Acid Ethyl Ester収率 78.5%

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

反応条件

温度
80 °C

実験手順

To a solution of ethyl (2-chloropyridin-3-yl)acetate (D. H. Bremner et al., Synthesis, 1997, 949) (8.0 g, 40.0 mmol) and carbon disulfide (3.18 g, 42.0 mmol) in DMSO (100 mL) was added sodium hydride portionwise (2.4 g, 60.0 mmol). After 60 minutes stifling at room temperature the mixture was heated at 80° C. for 2 hours. After this time the reaction mixture was allowed to cool to room temperature and methyl iodide (7.6 g, 54.0 mmol) added. After 18 hours ice (50 mL) was added and a yellow precipitate formed which was isolated via filtration to give the title compound as a grey solid (7.95 g, 78%). δH (DMSO-d6) 8.60 (1H, dd, J 1.6, 8.2 Hz), 8.46, (1H, dd, J 1.6, 4.6 Hz), 7.35 (1H, dd, J 4.6, 8.2 Hz), 4.48 (2H, q, J 7.1 Hz), 2.71, (3H, s), 1.49 (3H, t, J 7.1 Hz).

後処理

  1. temperatureto cool to room temperature
  2. customa yellow precipitate formed which
  3. customwas isolated via filtration

出典と根拠

ORDレコード
ord-43c760656bff4ce597814593e81e9710
出典データセット
uspto-grants-2013_12
特許番号
US08604051B2

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