Cesium carbonate → HCID 68770240, compound

Participants

Reaction Conditions

Reaction Steps

To a suspension of 5-hydroxyindole-2-carboxylate (5 g, 28.2 mmol), Cs2CO3 (20 g, 62.1 mmol) in DMSO (56 mL) was added 2-chlorobenzthiazole (3.5 mL, 4.8 g, 28.2 mmol) and the resulting reaction mixture was heated (70° C., 2 d). The reaction mixture was cooled (rt) and partitioned with H2O and EtOAc (50 mL each). The aqueous layer was treated with concentrated HCl to form a solid. The suspension was filtered and the solid washed with H2O and dried in vacuo to provide the title compound as a brown solid (7.55 g, 86%). 1H NMR (500 MHz, DMSO-d6): 12.03 (s, 1H), 7.88 (d, J=7.5, 1H), 7.73 (d, J=2.4, 1H), 7.67 (d, J=7.5, 1H), 7.55 (d, J=8.9, 1H), 7.43-7.40 (m, 1H), 7.31-7.28 (m, 2H), 7.15 (d, J=1.4, 1H), the CO2H proton was not detected.

Provenance & Evidence