Dimethylformamide → HCID 59252748, compound

Participants

Reaction Steps

Phosphorus oxychloride (0.01 mL, 0.11 mmol) was added to anhydrous DMF (0.5 mL) under argon. The mixture was stirred at rt for 15 min before 3-(1H-indol-5-yl)-2,2-dimethyl-3-phenyl-N-(thiazol-2-yl)propanamide (Example 101, 18 mg, 0.048 mmol) was added. The reaction mixture was stirred at rt for 1 hr. Aqueous sodium hydroxide solution (1N, 2 mL) was added, the mixture was stirred at 80° C. for 8 min. The reaction mixture was quenched with saturated aqueous ammonium chloride solution (1 mL) and water (1 mL) and extracted with dichloromethane (10 mL). The dichloromethane extract was dried (Na2SO4) and concentrated. Silica gel flash chromatography gave 3-(3-formyl-1H-indol-5-yl)-2,2-dimethyl-3-phenyl-N-(thiazol-2-yl)propanamide (Example 109, 16 mg, 0.04 mmol, 83% yield) as a glassy solid. MS found: (M+H)+=404. 1H NMR (400 MHz, CDCl3) δ ppm 9.93-9.95 (1 H, s) 9.92 (1H, s) 9.25 (1H, s) 8.34 (1H, s) 7.66 (1H, d, J=3.05 Hz) 7.34-7.39 (3 H, m) 7.12-7.28 (5H, m) 6.92 (1H, d, J=3.56 Hz) 4.51 (1H, s) 1.42 (6H, s).

Provenance & Evidence