Cesium carbonate → HCID 59577780, compound

Participants

Reaction Steps

To a suspension of 6-hydroxyindole (5.0 g, 37.6 mmol) and Cs2CO3 (36.7 g, 112.8 mmol) in MeCN (75 mL) was added 2-chlorobenzthiazole (6.4 g, 4.7 mL, 37.6 mmol) and the resulting suspension was stirred (rt, 2 d). The reaction mixture was partitioned with brine and EtOAc (200 mL each) and the aqueous layer was extracted with EtOAc (200 mL). The organic layers were combined, washed with brine (300 mL), dried, filtered and concentrated in vacuo. The resulting residue was purified by silica gel column chromatography using EtOAc:hexane (0-40%) to afford the title compound as a tan solid (6.1 g, 61%). MS (ESI): mass calcd. for C15H10N2OS, 266.3; m/z found, 267.1 [M+H]+. 1H NMR (400 MHz, CDCl3): 8.57 (s, 1H), 7.72 (dd, J=8.4, 0.6, 1H), 7.65-7.63 (m, 2H), 7.39-7.35 (m, 2H), 7.27-7.22 (m, 1H), 7.19-7.18 (m, 1H), 7.08 (dd, J=8.4, 2.1, 1H), 6.55-6.53 (m, 1H).

Provenance & Evidence