Cesium carbonate → (+/-)-2-(hydroxy(5-methoxy-7-methyl-1H-indol-4-yl)methyl)benzo[d]oxazole-5-carbonitrile

Participants

Reaction Conditions

Reaction Steps

A suspension of tert-butyl 4-((5-cyanobenzo[d]oxazol-2-yl)(hydroxy)methyl)-5-methoxy-7-methyl-1H-indole-1-carboxylate (1.10 g, 2.54 mmol) and Cs2CO3 (1.65 g, 5.08 mmol) in MeOH (25 mL) was allowed to stir at 60° C. for 4 h. The reaction mixture was cooled to rt and diluted with EtOAc (50 mL). The mixture was concentrated to half of the initial volume. The mixture was then diluted with brine and 1M aq. NaHSO4. The organic layer was separated. The aqueous layer was extracted with EtOAc. The combined organic phase was washed with brine, dried over Na2SO4, filtered, and concentrated. The residue was purified by flash column chromatography on silica gel (heptane/EtOAc=100:0 to 30:70) to give the title compound. 1H NMR (400 MHz, CD3OD) δ ppm 8.08 (t, J=1.07 Hz, 1H), 7.68 (s, 2H), 7.17 (d, J=3.15 Hz, 1H), 6.77 (s, 1H), 6.69 (s, 1H), 6.53 (d, J=3.15 Hz, 1H), 3.81 (s, 3H), 2.50 (s, 3H). HRMS calcd. for C19H15N3O3 (M+H)+ 334.1192. found 334.1191.

Provenance & Evidence