Potassium Carbonate → 1H-Indolamine

Participants

Reaction Steps

5-(2-Methanesulfonyloxy-ethyl)-2-methyl-1H-indole-3-carboxylic acid benzyl ester (0.300 g, 0.770 mmol, 1 eq, Example 56, Step D) was suspended in dioxane (20 mL) under Ar. K2CO3 (0.320 g, 2.320 mmol, 3 eq) was added followed by the addition of azetidine hydrochloride (0.217 g, 2.320 mmol, 3 eq). The reaction mixture was stirred and heated to reflux for 18 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). 0.030 g (11%) of the indole-amine was obtained as a white solid. This was converted to the .HCl salt. LC/MS (ESI+) 349 (M+1); Anal. Calcd for C22H24N2O2.1HCl.0.75H2O: C, 73.00; H, 7.10; N, 7.74; Found: C, 73.06; H, 6.95; N, 7.51.

Provenance & Evidence