1,2-Diaminocyclohexane, trans- → HCID 11244171, compound

Participants

Reaction Conditions

Reaction Steps

2-(1H-Pyrrol-3-yl)pyridine (300 mg, 2.0 mmol), 5-bromo-2-pyridin-2-ylbenzonitrile (538.7 g, 2.0 mmol), sodium tert-butoxide (384 mg, 4.0 mmol) and trans-1,2 diaminocyclohexane (23 mg, 0.2 mmol) were combined in DMF (10 mL) under argon. The reaction mixture was heated at 140° C. overnight. The reaction mixture was allowed to cool to ambient temperature. TLC analysis showed no starting material present. The reaction mixture was diluted with EtOAc (100 mL), and washed with H2O (3×100 mL), brine (100 mL), dried over Na2SO4, filtered, and concentrated in vacuo to afford a dark oil. The crude product was purified by column chromatography eluting with 5.5:4.5 EtOAc:Hexane to afford 2-pyridin-2-yl-5-(3-pyridin-2-yl-1H-pyrrol-1-yl)benzonitrile (160 mg, 27% yield) as a yellow solid. 1H NMR (CDCl3, 300 MHz) δ 8.73-8.74 (d, 1H), 8.48-8.49 (d, 1H), 8.14-8.15 (d, 1H), 7.98-8.01 (m, 3H), 7.92-7.94 (d, 1H), 7.86-7.88 (d, 1H), 7.79-7.81 (t, 1H), 7.47-7.53 (m, 2H), 7.22-7.24 (m, 1H), 6.94-6.95 (m, 1H). MS 323.4 (M++H).

Provenance & Evidence