Water → HCID 68770101, compound

Participants

Reaction Conditions

Reaction Steps

To a cooled (−78° C.) solution of [5-(benzothiazol-2-yloxy)-1-ethyl-1H-indole-2-carboxylic acid ethyl ester (1.05 g, 3.1 mmol) in THF (30 mL) was added LAH (1 M in THF, 0.8 mL, 0.72 g, 7.8 mmol) and the reaction mixture was stirred (−78° C., 1 h) and allowed to warm (rt, 12 h). The reaction mixture was treated with H2O (10 mL). The organic layer was separated and the aqueous layer was extracted with EtOAc (3×30 mL). The organic layer was dried, filtered and concentrated in vacuo. The resulting residue was purified by silica gel flash chromatography using MeOH:DCM (5-15%) to provide the title compound as a colorless foam (0.5 g, 49%). MS (ESI): mass calcd. for C18H16N2O2S, 324.0; m/z found, 325.1 [M+H]+. 1H NMR (500 MHz, DMSO-d6): 7.85 (d, J=7.2, 1H), 7.68 (d, J=7.6, 1H), 7.56 (s, 1H), 7.55 (d, J=6.4, 1H), 7.45-7.37 (m, 1H), 7.32-7.25 (m, 1H), 7.16 (dd, J=8.8, 2.4, 1H), 6.44 (s, 1H), 5.32 (s, 1H), 4.67 (s, 2H), 4.29 (q, J=7.1, 2H), 1.33 (t, J=7.1, 3H).

Provenance & Evidence