Potassium tert-butoxide → N-[3-(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 53 (3.82 g, 6.33 mmol) in THF (64 ml) was added a solution of potassium tert-butylate in THF (1 M, 9.49 ml, 9.49 mmol) at 0° C. The mixture was stirred at 0° C. for 1 hr, then an additional solution of potassium tert-butylate in THF (1 M, 2.00 ml, 2.00 mmol) was added and stirring was continued for an additional 1 hr. The reaction was quenched by addition of sat. aqueous NaHCO3 solution, and the mixture was extracted with EtOAc. The organic layer was dried, filtered, and evaporated to dryness. Purification by flash chromatography (silica gel, cyclohexane/EtOAc gradient) yielded Intermediate 54.

Provenance & Evidence