Sodium Carbonate → tert-butyl 1-(5-(5-(2,6-difluorophenyl)-1-tosyl-1H-pyrrolo[3,2-b]pyridin-3-yl)pyridin-3-yl)piperidin-4-ylcarbamate

Participants

Reaction Conditions

Reaction Steps

A solution of 5-(2,6-difluorophenyl)-3-iodo-1-tosyl-1H-pyrrolo[3,2-b]pyridine (92 mg, 0.180 mmol), crude tert-butyl 1-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-yl)piperidin-4-ylcarbamate (127 mg, 0.316 mmol) and Pd(PPh3)4 (20.83 mg, 0.018 mmol, Strem) in toluene (1 mL) and Ethanol (1.000 mL) was treated with Na2CO3, 2.0 M (0.180 mL, 0.361 mmol). The reaction vessel was capped, degassed and backfilled with argon; and the reaction was heated to 100° C. After 20 h, the solution was cooled to 23° C., diluted with EtOAc (100 mL) and washed with brine (75 mL), dried over MgSO4, concentrated in vacuo and purified by silica gel chromatography (eluent: 30-90% EtOAc/hexane), affording tert-butyl 1-(5-(5-(2,6-difluorophenyl)-1-tosyl-1H-pyrrolo[3,2-b]pyridin-3-yl)pyridin-3-yl)piperidin-4-ylcarbamate (85 mg, 71%). MS (ESI, pos. ion) m/z: 660.4 (M+1).

Provenance & Evidence