Sodium Carbonate → tert-butyl 4-(5-(3-(1-(3,5-difluorobenzyl)-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)pyridin-2-yl)piperazine-1-carboxylate

Participants

Reaction Steps

Using similar reaction conditions as described in step-ii of example-1, 5-bromo-3-(1-(3,5-difluorobenzyl)-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridine (STEP 1 example 71) (1 g, 1.515 mmol) was coupled with tert-butyl 4-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl)piperazine-1-carboxylate (intermediate 69C) (581 mg, 1.818 mmol) using sodium carbonate (481 mg, 4.545 mmol) and Pd(PPh3)2Cl2 (53 mg, 0.075 mmol) in toluene/ethanol/water (10/15/2 ml). This afforded 1.12 g (100% yield) of the titled compound after purification by column (Silica gel 60/120) using 40% ethyl acetate in hexane as eluent. MS: m/z=726.3 (M+1).

Provenance & Evidence