Morpholine → 1-methyl-6-morpholin-4-yl-1H-indole

Participants

Reaction Steps

An oven dried flask was flushed with argon and charged with 18-crown-6 (15 g, 56.7 mmol), 6-iodo-1-methyl-1H-indole (10.4 g, 40.46 mmol), morpholine (4.3 mL, 48.6 mmol), sodium t-butoxide (5.42 g, 54.7 mmol), tris(dibenzylidene acetone)dipalladium (0) (186 mg, 0.20 mmol) and 2,2′-bis(diphenylphosphino)-1,1-binaphthyl) (380 mg, 0.61 mmol). The flask was flushed with argon for 10 min and dry THF (80 mL) was added. The mixture was stilled at room temperature for 5 h, then diluted with ether and washed with brine. The organic layer was dried (MgSO4), evaporated and the crude product was purified by chromatography on silica gel using 5-30% ether/hexanes to give 1-methyl-6-morpholin-4-yl-1H-indole (8.17 g, 94%). [Ref: Wolfe, J. P.; Buchwald, S. L. J. Org. Chem. 1997, 62, 6066.]

Provenance & Evidence