Potassium Carbonate → 1H-Indolamine

Participants

Reaction Steps

5-(2-Chloro-ethoxy)-2-methyl-1H-indole-3-carboxylic acid benzyl ester (0.500 g, 1.450 mmol, 1 eq, Example 1, Step A) was suspended in dry acetonitrile (30 mL) under Ar. K2CO3 (0.400 g, 2.900 mmol, 2 eq) and KI (0.025 g, 0.145 mmol, 0.1 eq) were added followed by the addition of 1,3,3-trimethyl-6-azabicyclo-[3,2,1]octane (0.334 g, 2.180 mmol, 1.5 eq). The reaction mixture was stirred and heated to reflux for 24 hours. Then the reaction was quenched with saturated sodium bicarbonate and extracted with ethyl acetate (3×). The combined organic phases were washed with brine and dried over Na2SO4. After removing the solvent, the residue was loaded on silica gel and chromatographed, eluting with ethyl acetate/methanol/triethyl amine (100/10/1). 0.100 g (15%) of the indole-amine was obtained as a white solid. This was converted to the .HCl salt. LC/MS (ESI+) 461 (M+1); Anal. Calcd for C29H36N2O3.1 HCl.0.75H2O: C, 68.22; H, 7.60; N, 5.49; Found: C, 68.25; H, 7.41; N, 5.56.

Provenance & Evidence