Sodium Carbonate → tert-Butyl 6-(pyridin-4-yl)indoline-1-carboxylate

Participants

Reaction Conditions

Reaction Steps

To a 20 ml vial was added tert-butyl 6-bromoindoline-1-carboxylate 50.A (500 mg, 1.7 mmole), 4-pyridylboronic acid (309 mg, 2.5 mmol), tetrakis(triphenylphosphine) palladium(388, 0.34 mmol), DMF and 3 ml of saturated sodium carbonate. The reaction was stirred at 70° C. for 6 hours at which time the reaction mixture was partitioned between 300 ml EtAc and 200 ml of water. The organic solvent was removed by rotary evaporation and the crude product purified by reverse phase preparative HPLC to give tert-butyl 6-(pyridin-4-yl)indoline-1-carboxylate 50.B as a yellow solid (202 mg, 41% yield).

Provenance & Evidence