Water → HCID 16113673, compound

Participants

Reaction Conditions

Reaction Steps

3-chlorosulfonyl-benzoic acid (0.80 g, 0.36 mmol) was added in one portion to 1-(4-tert-butylbenzyl)-5-amino-1H-indole (0.30 g, 1.08 mmol) and diisopropylethylamine (0.25 g, 0.90 mmol) in acetone (25 ml) at 0° C. under a nitrogen atmosphere. The resulting yellow solution was stirred at 0° C. for 5 minutes and then stirred for 3 hours at room temperature. The reaction was quenched with water (2 ml) and concentrated in vacuo to a brown powder. The powder was partitioned between EtOAc (15 ml) and std NaHCO3 (10 ml). All organics were combined, extracted with water (10 ml) and brine (10 ml), dried with MgSO4, filtered and concentrated in vacuo to afford a brown powder. This brown powder was subjected to gradient RP-HPLC (H2O: CH3CN) and the title compound was isolated as a brown powder (0.36 g, 8.6% yield): MS (ESI) m/z 463, MS (ESI) m/z 461.

Provenance & Evidence