Thiophenol → 7,7-dimethyl-N-(tetrahydro-2H-pyran-2-yloxy)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine-2-carboxamide

Participants

Reaction Steps

To a mixture of 7,7-dimethyl-5-(2-nitrophenylsulfonyl)-N-(tetrahydro-2H-pyran-2-yloxy)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine-2-carboxamide (15.4 g, 31 mmol) and cesium carbonate (20.2 g, 62 mmol) in acetonitrile (800 mL) was added a solution of thiophenol (6.85 g, 62 mmol) in acetonitrile (70 mL). The reaction mixture was stirred at room temperature overnight. The solvent was removed in vacuo and the residue applied to silica gel chromatography (0-20% DCM/MeOH) to afford the title compound (8.2 g, 85%). LCMS (FA) ES+ 311; 1H NMR (400 MHz, DMSO) δ 11.49 (s, 1H), 7.30 (s, 1H), 4.91 (s, 1H), 4.01 (dd, J=15.6, 8.0 Hz, 1H), 3.71 (s, 2H), 3.55-3.44 (m, 1H), 2.71 (s, 2H), 1.69 (s, 3H), 1.53 (s, 3H), 1.25 (s, 6H).

Provenance & Evidence