Methanesulfonyl chloride → HCID 57504518, compound

Participants

Reaction Conditions

Reaction Steps

Butyllithium (1.6M in hexane, 1.668 mL, 2.67 mmol) was added dropwise to (3S)-3-(1-(2-chlorophenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-yloxy)pyrrolidin-2-one (Intermediate AC2) (800 mg, 2.43 mmol) in THF (15 mL) cooled to −78° C. under nitrogen. The resulting solution was allowed to warm to r.t., then recooled to −78° C. methanesulfonyl chloride (0.207 mL, 2.67 mmol) was added dropwise and the resulting solution was stirred at r.t. for 2 hours. The reaction mixture was quenched with water (20 mL) and extracted with ethyl acetate (2×50 mL). The combined organic layers were dried (MgSO4) and evaporated (995 mg). The crude product was purified by flash silica chromatography, eluting with 50 to 100% ethyl acetate in isohexane to afford the product (368 mg, 37.2%). 1H NMR (400 MHz, CDCl3) δ 2.35-2.47 (1H, m), 2.83-2.92 (1H, m), 3.37 (3H, s), 3.85-3.94 (1H, m), 4.06-4.16 (1H, m), 6.13 (1H, t), 7.44-7.56 (3H, m), 7.59-7.66 (1H, m), 8.32 (1H, s), 8.57 (1H, s); m/z (ES+) (M+H)+=408.29; HPLC tR=2.10 min.

Provenance & Evidence