Boron trifluoride etherate → 2,2-Dimethyl-propionic acid 5-bromo-3-(1,3-dihydro-isobenzofuran-1-yl)-pyrrolo[2,3-b]pyridin-1-ylmethyl ester

Participants

Reaction Steps

2,2-Dimethyl-propionic acid 5-bromo-3-[hydroxy-(2-hydroxymethyl-phenyl)-methyl]-pyrrolo[2,3-b]pyridin-1-ylmethyl ester (1.60 g, 3.58 mmol) was dissolved in anhydrous dichloromethane (80 ml), and the mixture was stirred at room temperature. Boron trifluoride etherate (374 ul, 2.97 mmol) was added and the mixture stirred for 20 minutes. The reaction was quenched with saturated sodium bicarbonate solution. The organic layer was separated, and the aqueous layer was washed with dichloromethane. The organic layers were combined, dried over magnesium sulfate, and the mixture was concentrated in vacuo. The crude material was purified by flash chromatography (0-100% ethyl acetate in hexanes) to give 1.29 g (84%) of 2,2-dimethyl-propionic acid 5-bromo-3-(1,3-dihydro-isobenzofuran-1-yl)-pyrrolo[2,3-b]pyridin-1-ylmethyl ester. MS: m/z 429.2+431.2 (M+H+).

Provenance & Evidence