Ethylenediamine → 3-(2,5-Dihydro-1H-imidazol-2-ylmethyl)-1-methanesulfonyl-1H-pyrrolo[2,3-b]pyridine

Participants

Reaction Conditions

Reaction Steps

Carbon disulfide (2 drops) and (1-Methanesulfonyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-acetonitrile (4) (81 mg, 0.34 mmol) was added sequentially in this order to ethylenediamine (2 ml). The reaction was heated at 140° C. for 30 minutes and concentrated under reduced pressure. The residue was chromatographed over silica gel eluting with 92:8:1 ethyl acetate:methanol:ammonium hydroxide to obtain 3-(2,5-Dihydro-1H-imidazol-2-ylmethyl)-1-methanesulfonyl-1H-pyrrolo[2,3-b]pyridine (50 mg, 53%). 1H NMR (DMSO-d6) δ: 3.40 (4H, s), 3.70 (3H, s), 7.37 (1H, dd, J=4.7 Hz, 7.9 Hz), 7.64 (1H, s), 8.11 (1H, dd, J=1.5 Hz, 7.9 Hz), 8.42 (1H, dd, J=1.5 Hz, 4.7 Hz); M+H 279.

Provenance & Evidence