Boron tribromide → 2,6-Dimethyl-4-(5-(1-phenyl-cyclopropyl)thiazolo[5,4-b]pyridin-2-yl)phenol

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Reaction Conditions

Reaction Steps

Boron tribromide (1.0M in DCM; 963 μl, 0.963 mmol) was added to a solution of 2-(4-(benzyloxy)-3,5-dimethylphenyl)-5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridine (247.4 mg, 0.535 mmol) in DCM (24.0 mL) at −78° C., and the resulting solution was stirred at −78° C. for 5 min. Excess BBr3 was then quenched by the addition of water (50 mL), and the resulting mixture was diluted with DCM (100 mL) and allowed to warm to 25° C. The organic layer was separated, dried over sodium sulfate, filtered, and concentrated in vacuo. Chromatographic purification of the residue (silica gel, 0-100% ethyl ether/hexanes) afforded 2,6-dimethyl-4-(5-(1-phenyl-cyclopropyl)thiazolo[5,4-b]pyridin-2-yl)phenol as a white solid. MS (ESI) m/z: Calculated: 372.1; Observed: 373.2 (M++1).

Provenance & Evidence