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

HRID 2061456

반응식

HRID 2061456 반응식
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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

실험 절차

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 stirring 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).

후처리

  1. temperaturewas heated at 80° C. for 2 hours
  2. temperatureto cool to room temperature
  3. customa yellow precipitate formed which
  4. customwas isolated via filtration

출처 및 근거

ORD 기록
ord-dfc556b094de4f919023b98aab2e9b04
출처 데이터셋
uspto-grants-2012_10
특허 번호
US08283359B2

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