Methylamine → 2-Methyl-5-(2-methylamino-ethyl)-1H-indole-3-carboxylic Acid Benzyl Ester

Participants

Reaction Steps

A mixture of 5-(2-methanesulfonyloxy-ethyl)-2-methyl-1H-indole-3-carboxylic acid benzyl ester (500 mg, 1.29 mmol, Example 56, Step D) in 29% methylamine in ethanol solution (6 mL) was stirred at room temperature overnight and then partitioned between methylene chloride and water. The organic phase was washed with water and brine, dried over Na2SO4 and filtered. The filtrate was concentrated in vacuo to give a residue, which was triturated with diethyl ether to give 410 mg (99%) of the desired product as a white foam: mp 65-68° C.; MS(APCI+): m/z 323.1 (MH+); Anal. Calcd for C20H22N2O2.0.5H2O: C, 72.48; H, 7.00; N, 8.45. Found: C, 72.21; H, 6.85; N, 8.34.

Provenance & Evidence