2-Chloro-3-nitropyridine → (R)-5-(3-Nitropyrid-2-ylamino)-3-(pyrrolidin-2-ylmethyl)-1H-indole

Participants

Reaction Steps

(R)-5-Amino-3-(pyrrolidin-2-ylmethyl)indole and 2-chloro-3-nitropyridine were used. Sodium acetate was used as base, acetic acid was used as solvent, and the reaction was heated at reflux (116°0 C.) for 2 hours. Column chromatography afforded the title compound (23%) as a dark red foam: 1H NMR (CDCl3) δ 10.05 (br s, 1H), 9.23 (br s, 1H), 8.49 (dd, J=1.8 and 8.3 Hz, 1H), 8.39 (1.8 and 4.5 Hz, 1H), 7.70 (d, J=1.7 Hz,1H), 7.33-7.22 (m, 2H), 6.98 (s,1H), 6.73 (dd, J=4.5 and 8.3 Hz, 1H), 3.46-3.34 (m, 1H), 3.10-2.97 (m, 1H), 2.97-2.78 (m, 3H), 1.99-1.64 (m, 3H), 1.56-1.42 (m, 1H); 13C NMR (CDCl3) δ 155.7, 151.5, 135.5, 134.5, 129.2, 128.1, 127.8, 123.8, 119.4, 114.3, 113.0, 111.6, 59.5, 45.7, 31.3, 30.6, 24.7; FAB LRMS (m/z, relative intensity) 338 (6, [MH+ ]), 309 (12), 155 (49), 135 (38), 119 (100). Anal. calcd for C18H19N5O2.0.67 C2H4O2 [acetic acid]: 61.53; H, 5.79; N, 18.56. Found: C, 61.57; H, 5.74; N, 18.82.

Provenance & Evidence