Methanesulfonyl chloride → HCID 86707735, compound

Participants

Reaction Steps

To a solution of ethyl 2-(6-phenylbenzo[d]thiazol-2-yl)acetate (390 mg, 1.3 mmol) (described in WO 2011/074560) in DMF (4 mL) at 0° C. was added DBU (0.49 mL, 3.3 mmol) and the reaction mixture was stirred at rt for 10 min. Methanesulfonyl chloride (0.12 mL, 1.6 mmol) was added dropwise and the mixture stirred for 0.5 h. Additional methanesulfonyl chloride (0.030 mL, 0.40 mmol) was added and the reaction mixture stirred for 10 min. The reaction mixture was diluted with H2O then extracted with EtOAc (3×), dried (Na2SO4), filtered and concentrated under reduced pressure. The residue was purified by silica gel chromatography eluting with 0 to 100% EtOAc/hexane to give Compound 89a (360 mg, 73% yield) as yellow powder. RT=2.06 min using analytical method (Q), 376.9 (M+H). 1H NMR (500 MHz, CDCl3) δ 7.88-7.75 (m, 1H), 7.68-7.53 (m, 3H), 7.53-7.34 (m, 5H), 4.42 (qd, J=7.2, 3.0 Hz, 2H), 3.39-3.21 (m, 3H).

Provenance & Evidence