Pyridine → HCID 59596285, compound

Participants

Reaction Steps

To [3-(3-bromo-phenyl)-3-(4-hydroxy-phenyl)-3H-isoindol-1-yl]-carbamic acid tert-butyl ester (Scheme #6, S) (900 mg, 1.88 mmol) in tetrahydrofuran (10 mL) was added pyridine (306 uL, 3.76 mmol) and methanesulfonyl chloride (218 uL, 2.82 mmol). After stirring over night, additional pyridine (306 uL, 3.76 mmol) and methanesulfonyl chloride (218 uL, 2.82 mmol) were added and the reaction allowed to stir for 8 hours. The solvent was removed under reduced pressure and the resulting oil put under high vacuum. The crude material was chromatographed on 20 g silica gel eluting with 2.5% methanol/dichloromethane and the combined purified fractions removed of solvent to give the title compound as a white solid (734 mg, 70%). 1H NMR (500 MHz, DMSO-d6/TFA-d) δ 8.67 (d, J=8.0 Hz, 1 H), 7.92 (t, J=7.6 Hz, 1 H), 7.84 (d, J=7.8 Hz, 1 H), 7.78 (t, J=7.7 Hz, 1 H), 7.62 (d, J=7.6 Hz, 2 H), 7.49 (d, J=8.7 Hz, 2 H), 7.39-7.33 (m, 4 H), 3.40 (s, 3 H), 1.63 (s, 9 H); MS (ES+) m/z 557 [M+1]+; tR=2.29 min.

Provenance & Evidence