Carbon tetrabromide → HCID 54674389, compound

Participants

Reaction Steps

A solution of (R)-N-(1-cyclohexylethyl)-6-(hydroxymethyl)nicotinamide (3.2a, 262 mg, 1 mmol) and Ph3P (472 mg, 1.8 mmol) in CH2Cl2 (10 mL) was cooled to 0° C. and a solution of CBr4 (463 mg, 1.4 mmol) in CH2Cl2 (2 mL) was added dropwise. The reaction was allowed to warm to rt and was stirred overnight. The reaction was concentrated under reduced pressure and the residue purified by column chromatography (silica gel) using 0-40% EtOAc/hexanes to afford 3.3a (156 mg): 1H-NMR (400 MHz, CDCl3) δ 8.91 (s, 1H), 8.11 (dd, J1=8.0 Hz, J2=2.0 Hz, 1H), 7.53 (d, J=8.0 Hz, 1H), 5.98 (d, J=8.0 Hz, 1H), 4.59 (s, 2H), 4.15-4.07 (m, 1H), 1.84-1.68 (m, 5H), 1.49-1.43 (m, 1H), 1.29-1.03 (m, 8H); LC-MS (220 nm), >98%, 325.2 and 327.2 [M+H].

Provenance & Evidence