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

HRID 1911092

Reaction equation

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]

Participants

Conditions

Temperature: 80 °C

Procedure

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).

Workup

temperatureto cool to room temperature
customa yellow precipitate formed which
customwas isolated via filtration

Sources & evidence

ORD record: ord-43c760656bff4ce597814593e81e9710
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08604051B2

Linked notes

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