Dimethylformamide → HCID 68183342, compound

Participants

Reaction Conditions

Reaction Steps

To a 20 mL vial was added a solution of 2-bromo-4-(4-chlorophenyl)-5,6-dihydrothieno[2,3-c]pyridin-7(4H)-one (0.0800 g, 0.233 mmol) in anhydrous N,N-dimethylformamide (3.00 mL, 38.7 mmol) and cooled to 0° C. NaH 60% in mineral oil (60:40, sodium hydride:Mineral Oil, 0.0500 g, 1.25 mmol) was added in portions and stirred for 10 minutes. Methyl iodide (0.0876 mL, 1.41 mmol) was added and the reaction mixture was slowly warmed to room temperature and allowed to stir for 1 hour. The reaction was quenched by the addition of a saturated aqueous solution of ammonium chloride (5.00 mL) and diluted with EtOAc (10.00 mL). The mixture was successively washed with water (10.0 mL×2) and brine (10.0 mL). The organic layer was dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The crude material was wet loaded onto silica gel and then purified using a ISCO (4 g cartridge, gradient hexanes to 75% EtOAc over 30 min) to afford the product (0.0812 g, 78%) as a yellow oil. LC/MS (AA) ES+ 356, 358, 360. 1H NMR (dmso-d6, 400 MHz): d 7.43-7.37 (2H, m), 7.25-7.19 (2H, m), 6.98 (1H, s), 3.81-3.73 (1H, m), 3.66-3.58 (1H, m), 2.85 (3H, s).

Provenance & Evidence