Ethyl Acetate → HCID 10134266, compound

Participants

Reaction Conditions

Reaction Steps

5-Hydroxy-2-methyl-1H-indole-3-carboxylic acid benzyl ester (5.0 g, 17.8 mmol), K2CO3 (6.14 g, 44.4 mmol), KI (0.029 g, 1.78 mmol) and N(chloroethyl)cyclopentyl hydrochloride (3.02 g, 17.8 mmol) were mixed together in MEK (100 mL) and refluxed at 80° C. for 72 hours. The reaction was then permitted to cool and diluted with ethyl acetate. Then solution was washed with deionized water and brine, dried on Na2SO4, filtered and concentrated under reduced pressure. The resulting crude mixture was then chromatographed (10% MeOH/CH2Cl2) to give 1.20 g (26.8%) of the desired ester as a white solid, mp 110-116° C. 1HNMR (400 MHz, DMSO): δ 1.64 (b,4H), 2.45 (b, 4H), 2.59 (s, 3H, ArCH3), 4.00 (m, 2H), 5.27 (s, 2H), 6.70 (dd, J=8.54 Hz, J=2.44 Hz, 1H), 7.15 (d, J=8.79 Hz, 1H), 7.28-7.47 (m, 5H), 11.71 (s, NH); MS(APCI+) m/z 379.1(MH+). Anal. Calcd for C23H26N2O3.0.42H2O: C, 71.56;H, 7.01; N, 7.26. Found: C, 71.36: H, 6.93: N, 7.04; IR(KBr): 3371, 2909, 1665, 1481, 1448, 1178, 1087 cm−1.

Provenance & Evidence