Methanol → HCID 44465845, compound

Participants

Reaction Conditions

Reaction Steps

2-Isopropyl-1-(4-methoxy-phenyl)-1H-indole-3-carbonitrile (3 mg, 0.01 mmol) was dissolved in dry CH2Cl2 (0.5 ml) and stirred at 0° C. BBr3 (1M in CH2Cl2, 50 μl) was added and the mixture left in the fridge with stirring overnight. Some drops of MeOH were added and stirred. The solvent was removed in vacuo and the mixture partitioned in H2O/DCM. The organic phase was separated using a phase separator. The solvent was removed in vacuo and the mixture was chromatographed using a prepacked silica column (solvent: EtOAc:n-Heptane 3-7) to afford the desired 1-(4-hydroxy-phenyl)-2-isopropyl-1H-indole-3-carbonitrile (1.1 mg, 39%). 1H NMR (acetone-d6, 500 MHz): 7.64 (m, 1H), 7.32 (m, 2H), 7.28 (m, 1H), 7.22 (m, 1H), 7.11 (m, 2H), 6.98 (m, 1H), 3.07 (m, 1H) and 1.43 (d, 6H, J=7.0 Hz).

Provenance & Evidence