Dichloromethane → (S)-ethyl 2-(tert-butoxy)-2-(7-(4-chlorophenyl)-2-(1,2-dimethyl-1H-benzo[d]imidazol-6-yl)-5-methylbenzo[d]thiazol-6-yl)acetate

Participants

Reaction Conditions

Reaction Steps

A microwave vial was charged with 6-bromo-1,2-dimethyl-1H-benzo[d]imidazole (150 mg, 0.67 mmol), Bis(pinacolato)diboron (189 mg, 0.74 mmol), PdCl2(dppf).CH2Cl2 (55 mg, 0.07 mmol), then KOAc (221 mg, 2.25 mmol). The vial was flushed with argon, diluted with dioxane (3 mL), sealed, then heated to 100° C. for 45 minutes. The reaction mixture was allowed to cool to room temperature and then a portion of this cooled solution (1.0 mL, 0.22 mmol) was added to a vial that was charged with (S)-ethyl 2-(2-bromo-7-(4-chlorophenyl)-5-methylbenzo[d]thiazol-6-yl)-2-tert-butoxyacetate (55 mg, 0.10 mmol) and Pd(PPh3)4 (12 mg, 0.01 mmol). The mixture was diluted with dioxane (1.5 mL) and to this was added 2M aqueous K2CO3 (0.21 mL, 0.42 mmol). The vial was sealed, heated to 100° C. for 1 hour, and then allowed to cool to room temperature. The mixture was diluted with EtOAc, dried over Na2SO4, filtered through a small pad of silica gel, and concentrated in vacuo to afford the desired product. LCMS-ESI+: calc'd C31H33ClN3O3S: 562.2 (M+H+); Found: 562.3 (M+H+).

Provenance & Evidence