Methanol → HCID 58381984, compound

Participants

Reaction Steps

A solution of 7-(5-methoxy-1-methyl-1H-indol-3-yl)-1-methyl-6-tosyl-1,6-dihydropyrazolo[3,4-d]pyrrolo[2,3-b]pyridine (0.22 g, 0.46 mmol, [WO2009/152133, Example #42]) in DCM (10 mL) was cooled to about 0° C. BBr3 (1.0 M in DCM, 1.39 mL, 1.39 mmol) was added dropwise. The mixture was stirred at rt for about 16 h. The mixture was cooled to about 0° C. and MeOH (0.5 mL) was added dropwise followed by a solution of saturated aqueous NaHCO3 (6 mL). The mixture was concentrated in vacuo and the residue was partitioned between EtOAc (2×75 mL) and saturated aqueous NaHCO3 (50 mL). The organic layer was isolated and washed with saturated aqueous NaHCO3 (50 mL), brine (50 mL), dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue was purified by flash chromatography (12 g silica gel column, EtOAc/MeOH/Et3N 100:10:0 to 100:10:1) to give 1-methyl-3-(1-methyl-6-tosyl-1,6-dihydropyrazolo[3,4-d]pyrrolo[2,3-b]pyridin-7-yl)-1H-indol-5-ol (0.21 g, 99%): LC/MS (Table 2, Method a) Rt=2.10 min; MS m/z 472 (M+H)+.

Provenance & Evidence