Diphenyl Ether → benzyl 2,4-bis(benzyloxy)-5-ethyl-6-(6-methoxy-1H-indol-2-yl)nicotinate

Participants

Reaction Conditions

Reaction Steps

A mixture of (1-(tert-butoxycarbonyl)-6-methoxy-1H-indol-2-yl)boronic acid (437 mg, 1.5 mmol), Pd2dba3 (23 mg, 0.025 mmol), KF (174 mg, 3.0 mmol), t-Bu3PHBF4 (17.4 mg, 0.06 mmol) and benzyl 2,4-bis(benzyloxy)-6-chloro-5-ethylnicotinate (488 mg, 1.0 mmol) in THF (2.0 mL) was stirred at 60° C. under argon overnight. The solvent was then replaced with diphenyl ether (2.0 mL) and the mixture was stirred at 180° C. for 1 h. After cooling, the reaction mixture was loaded on a silica gel column and the product was eluted with ethyl acetate in hexanes (0-30% gradient) to furnish benzyl 2,4-bis(benzyloxy)-5-ethyl-6-(6-methoxy-1H-indol-2-yl)nicotinate (380 mg) in 64% yield.

Provenance & Evidence