Sodium borohydride → HCID 59441716, compound

Participants

Reaction Steps

A yellow slurry of 5-(methyloxy)-1-[(4-methylphenyl)sulfonyl]-6-nitro-2,3-dihydro-1H-indole (16.1 g, 46 mmol) and NiCl2.6H2O (3.29 g, 13.9 mmol) in THF (150 mL) and MeOH (300 mL) was treated with NaBH4 (5.2 g, 139 mmol) in small portions. The resulting mixture was stirred for 1 h, concentrated onto Celite and purified by column chromatography using 0-10% MeOH (containing 0.2% NH3)/CH2Cl2to obtain 5-(methyloxy)-1-[(4-methylphenyl)sulfonyl]-2,3-dihydro-1H-indol-6-amine as white solid (11.94 g, 81%). 1H NMR (400 MHz, DMSO-d6) δ ppm 2.33 (s, 3H), 2.63 (t, J=8.15 Hz, 2H), 3.66 (s, 3H), 3.77 (t, J=8.06 Hz 2H), 4.79 (s, 2H), 6.58 (s, 1H), 6.94 (s, 1H), 7.34 (d, J=7.87 Hz, 2H), 7.62 (d, J=7.87 Hz, 2H); ESIMS (M+H)+=320.12.

Provenance & Evidence