Chlorosuccinimide → HCID 178489080, compound

Participants

Reaction Steps

To a solution of (−)-2-(1-hydroxy-1-(5-methoxy-7-methyl-1H-indol-4-yl)ethyl)-1H-benzo[d]imidazole-5-carbonitrile (Example 26-C) (20 mg, 0.058 mmol) in DMF (0.58 mL) was added NCS (14 mg, 0.1 mmol) at 0° C. The reaction was stirred in the ice bath for 1 hour. At this point, the reaction was quenched with a saturated solution of aq. Na2S2O3 at 0° C., and then the mixture was extracted with EtOAc and then the EtOAc layer was dried, concentrated, absorbed onto silica and purified by flash column chromatography (0-100% EtOAc in heptanes) to provide the title compound. 1H NMR (400 MHz, DMSO-d6) δ ppm 12.18-12.43 (m, 1H) 11.29 (br. s., 1H) 8.06 (s) 7.65-7.79 (m) 7.45-7.52 (m) 7.43 (d, J=3.03 Hz, 1H) 6.72 (s, 1H) 5.78-6.09 (m, 1H) 3.16 (s, 3H) 2.42 (s, 3H) 2.15 (s, 3H). HRMS calcd. for C20H17ClN4O2 (M+H)+ 381.1113. found 381.1123.

Provenance & Evidence