Lithium Chloride → HCID 58209539, compound

Participants

Reaction Conditions

Reaction Steps

Pd(Ph3P)4 (0.115 g, 0.099 mmol) was added to a mixture of tributyl(ethynyl)stannane (1.539 g, 4.88 mmol), (S)-tert-butyl 2-(4-(4-bromophenyl)-1H-imidazol-2-yl)pyrrolidine-1-carboxylate (0.965 g, 2.46 mmol; for its preparation, see PCT Publication No. WO 2008/021927) and LiCl (0.277 g, 6.53 mmol) in dioxane (20 mL) in a sealed pressure tube. The mixture was purged with nitrogen, sealed and heated at 80° C. for 3 hr. After it was allowed to cool to ambient temperature, the volatile component was removed in vacuo and the residue was partitioned between CH3CN and hexanes (2:1 ratio in volume). The hexane layer was washed with an equal volume of CH3CN. The combined CH3CN phase was rotervaped, and the resultant crude material was purified with a BIOTAGE® (100 g silica gel; 40-50% EtOAc/hexanes) to afford Intermediate M1a as a dull orange solid (591 mg). 1H NMR (DMSO-d6, δ=2.50 ppm, 400 MHz): 12.21/11.95/11.88 (three ‘br s’, 1H), 7.74 (d, J=8.3, 1.6H), 7.66-7.47 (m, 1.66H), 7.41 (d, J=8.3, 1.6H), 7.32 (m, 0.14H), 4.84-4.75 (m, 1H), 4.19/4.12 (two ‘s’, 1H), 3.52 (m, 1H), 3.39-3.29 (m, 1H), 2.28-1.77 (m, 4H), 1.39/1.15 (two ‘s’, 9H). LC/MS: Anal. Calcd. for (M+H)+ C20H24N3O2: 338.18. Found, 338.28.

Provenance & Evidence