1,2-Dibromo-1,1,2,2-tetrachloroethane → N-[3-(7-Benzenesulfonyl-6-bromo-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-2-methyl-phenyl]-4-tert-butyl-benzamide

Participants

Reaction Conditions

Reaction Steps

To a solution of Intermediate 52 (4.26 g, 8.12 mmol) in THF (150 ml) at −78° C. was added LDA (1.5 M in THF, 16.24 ml, 24.36 mmol) slowly. The resulting mixture was stirred for 1.5 hrs at −78° C. before adding a solution of 1,2-dibromo-tetrachloroethane (3.97 g, 12.18 mmol) in THF (1 ml). Stirring was continued at −78° C. for 2 hrs, then the reaction mixture was quenched by addition of sat. aqueous NH4Cl solution and warmed up to r.t. The mixture was extracted with EtOAc and the organic layer was dried, filtered, and evaporated to dryness. Purification by flash chromatography (silica gel, cyclohexane/EtOAc gradient) yielded Intermediate 53.

Provenance & Evidence