Boron tribromide → HCID 57845448, compound

Participants

Reaction Steps

To a solution of methyl(1-acetyl-6-methoxy-1H-indol-3-yl)acetate (0.67 g, 2.56 mmol) (Example 13) in dichloromethane (10 mL) was added 1 M BBr3 in dichloromethane (10.3 mL, 10.3 mmol) at −78° C. under argon. Stirring was continued at −78° C. for 1 h, at 0° C. for 3 h and at rt for 18 h consecutively. The reaction mixture was quenched with water and dichloromethane was added. Solid NaHCO3 was added to adjust the pH of the mixture to 8. The mixture was extracted with CH2Cl2. The combined organic layers were dried over MgSO4, filtered, and concentrated to yield a yellow solid (200.0 mg, 32%). LC/MS m/z 248 (M+H)+; 1H NMR (400 MHz, DMSO-d6) 9.42 (s, 1H), 7.77 (d, 1H), 7.52 (s, 1H), 7.28 (d, 1H), 6.71 (dd, 1H), 3.71 (s, 2H), 3.61 (s, 3H), 2.55 (s, 3H).

Provenance & Evidence