Boron tribromide → HCID 178461938, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of [(S)-1-[1-(cis-3-benzyloxycyclobutyl)-6-fluoro-1H-benzoimidazol-2-yl]ethyl]-(9H-purin-6-yl)amine (0.12 g, 0.26 mmol) in DCM (5 mL) cooled to 0° C. To this mixture was added boron tribromide (1M in DCM, 0.53 mL, 0.53 mmol) dropwise and the resultant mixture stirred at RT for 2 h. The reaction mixture was quenched with MeOH (2 mL) and concentrated in vacuo. The resulting yellow was solid purified by column chromatography (Si—PCC, gradient 0-10% MeOH in DCM) to afford 391 as an off-white glassy solid (50 mg, 50%). LCMS (Method K): RT 2.21 min [M+H]+ 368.3. 1H NMR (DMSO-d6): δ 12.8 (1H, br s), 8.21 (1H, s), 8.09 (1H, s), 7.78-7.89 (1H, m), 7.47-7.61 (2H, m), 6.95-7.04 (1H, m), 5.78 (1H, br s), 5.43 (1H, qn, J=8.82 Hz), 5.11 1H, d, J=4.2 Hz), 4.41-4.50 (1H, m), 2.86-3.04 (2H, m), 2.26-2.38 (1H, m), 2.08-2.20 (1H, m), 1.59 (1H, d, J=6.7 Hz)

Provenance & Evidence