Carbon tetrabromide → HCID 11699537, compound

Participants

Reaction Steps

To a solution of 2-[4-({3-chloro-4-[(3-fluorobenzyl)oxy]phenyl}amino) [1]benzothieno[2,3-d]pyrimidin-7-yl]ethanol (700 mg, 1.46 mmol, 1 equiv) in THF (10 mL) were added triphenylphosphine (0.82 g, 3.12 mmol, 3 equiv) and carbon tetrabromide (1.03 g, 3.12 mmol, 3 equiv). The resulting solution was stirred at rt for 14 h and the solvent was evaporated under reduced pressure. The resulting crude material was purified by flash chromatography eluting with 9:1 CH2Cl2/EtOAc yielding a light yellow solid (688 mg, 1.27 mmol, 87%). 1H-NMR (CDCl3) δ 8.60 (s, 1H), 7.96 (d, J=8.6 Hz, 1H), 7.81 (s, 1H), 7.75 (d, J=2.7 Hz, 1H), 7.50-7.44 (m, 3H), 7.39-7.34 (m, 1H), 7.23 (m, 2H), 7.03 (td, 1H), 7.00 (d, J=9.0 Hz, 1H), 5.12 (s, 2H), 3.68 (t, 2H), 3.36 (t, 2H); LCMS RT=4.26 min, [M+H]+=541/544

Provenance & Evidence