Water → HCID 49832489, compound

Participants

Reaction Conditions

Reaction Steps

To a cooled (−78° C.) solution of [5-(benzothiazol-2-yloxy)-1H-indol-2-yl]-piperidin-1-yl-methanone (150 mg, 0.40 mmol) in THF (5 mL) was added LAH (2 M in THF, 0.2 mL, 18 mg, 0.40 mmol) and the reaction mixture was stirred (−78° C., 1 h) and allowed to warm (rt, 1 h). The reaction mixture was cooled (0° C.) and treated with H2O (5 mL). The organic layer was separated and the aqueous layer was extracted with EtOAc (3×15 mL). The organic layer was dried, filtered and concentrated in vacuo. The resulting residue was purified by silica gel flash chromatography using MeOH:DCM (0-8%) to provide the title compound as a colorless foam (78 mg, 54%). MS (ESI): mass calcd. for O21H21N3OS, 363.1; m/z found, 364.1 [M+H]+. 1H NMR (400 MHz, CDCl3): 8.64 (s, 1H), 7.77-7.70 (m, 1H), 7.61 (dd, J=7.9, 0.7, 1H), 7.48 (d, J=2.3, 1H), 7.40-7.32 (m, 2H), 7.22 (dd, J=11.0, 4.3, 1H), 7.10 (dd, J=8.7, 2.4, 1H), 6.35 (s, 1H), 3.62 (s, 2H), 2.60-2.30 (m, 4H), 1.65-1.54 (m, 4H), 1.53-1.41 (m, 2H).

Provenance & Evidence