Boron tribromide → HCID 24994651, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 1-methylethyl 4-({[6-(4-{[2-(methoxy)ethyl]sulfonyl}phenyl)-3-pyridinyl]oxy}methyl)-1-piperidinecarboxylate (Example 81, 0.13 g, 0.27 mmol) in CH2Cl2 (10 mL) was treated with BBr3 (1.0M in CH2Cl2, 1.64 mL, 1.64 mmol) at −78° C. The reaction mixture was allowed to warm up to 10° C., and poured onto ice and aqueous NaHCO3. The mixture was extracted with EtOAc. The organic extracts were combined and washed with brine, dried over Na2SO4, filtered, and the filtrate was concentrated to give the crude product as a brown solid. The crude product was purified by chromatography on a silica gel column eluted with 2:4:0.1 EtOAc/CH2Cl2/MeOH to give 66 mg (53%) of the title compound as an off-white solid. 1H NMR (400 MHz, CD3OD): δ 8.36 (d, 1H, J=2.9 Hz), 8.17 (d, 2H, J=8.5 Hz), 8.00 (d, 2H, J=8.3 Hz), 7.92 (d, 1H, J=8.8 Hz), 7.49 (dd, 1H, Ja=8.8 Hz, Jb=2.9 Hz), 4.90-4.80 (m, 1H), 4.25-4.10 (m, 2H), 3.99 (d, 2H, J=6.1 Hz), 3.88 (t, 2H, J=6.2 Hz), 3.42 (t, 2H, J=6.2 Hz), 2.95-2.75 (m, 2H), 2.15-2.00 (m, 1H), 1.95-1.80 (m, 2H), 1.35-1.20 (m, 8H); LRMS (ESI), m/z 463 (M+H).

Provenance & Evidence