Dimethylformamide → N-{2-Bromo-6-methyl-3-[3-(methyloxy)phenyl]thieno[2,3-b]pyridin-4-yl}cyclopropanesulfonamide

Participants

Reaction Steps

To a stirred solution of 2-bromo-6-methyl-3-[3-(methyloxy)phenyl]thieno[2,3-b]pyridin-4-amine (Description 17) (303 mg, 0.868 mmol) in THF (5 mL) at RT, was added sodium tert-butoxide (214 mg, 2.227 mmol). The reaction mixture was stirred at RT for 15 min, followed by the addition of cyclopropanesulfonyl chloride (0.16 mL, 1.74 mmol). The reaction mixture was stirred at RT for 1.5 h, followed by the sequential of addition of DMF (2.5 mL), sodium tert-butoxide (202 mg) and cyclopropanesulfonyl chloride (0.16 mL, 1.741 mmol). The reaction mixture was stirred at RT for another 1.5 h, followed by the addition of water (25 mL) and ethyl acetate (25 mL). The aqueous layer was separated and extracted with ethyl acetate (3×25 mL). The combined organic extracts were washed with water (15 mL), dried (phase separating column) and concentrated to give a residue, which was purified on silica, eluting with a gradient of 0-75% ethyl acetate in cyclohexane, to give a residue (127 mg). Ca. 45 mg of this material was purified further by MDAP (acidic conditions) followed by trituration with diethyl ether, to give the title compound (9 mg). LCMS (A) m/z: 453/455 [M+1]+, Rt 1.50 min (acidic).

Provenance & Evidence