Dimethylformamide → Ammonium Hydroxide

Participants

Reaction Steps

A solution of 2-[2-(7-Chloro-thieno[3,2-b]pyridin-2-yl)-thiazol-4-yl]-propan-2-ol (100 mg, 0.322 mmol), DMF 0.7 mL, cesium carbonate (210 mg, 0.644 mmol) and 2-methyl-1H-indol-5-ol and (95.0 mg, 0.644 mmol) was heated to 85° C. for sixteen hours. The reaction mixture was cooled to room temperature and extracted with 5% methanol/ethyl acetate and water. The layers were separated, and the aqueous layer was washed with a 5% methanol and ethyl acetate solution. The combined organic layers were washed with brine, dried over magnesium sulfate, and evaporated under reduced pressure to give an oily brown solid. Silica gel chromatography (98:1.8:0.2 CHCl3:CH3OH:NH4OH) afforded the titled compound (46 mg) as an off-white solid in 17% yield. C22H19N3O2S2: APCI m/z 422.2 (pos.); 1H NMR (CD3OD): δ 8.38 (d, 1H, J=5.6 Hz), 7.89 (s, 1H), 7.47 (s, 1H), 7.35 (d, 1H, J=8.7 Hz), 7.26 (s, 1H), 6.87 (d, 1H, J=8.7 Hz), 6.57 (d, 1H, J=5.6 Hz), 6.17 (s, 1H), 2.43 (s, 3H), 1.61 (s, 6H) ppm.

Provenance & Evidence