Water → 5-(2,6-diethyl-phenyl)-1-(1-propyl-butyl)-1H-pyrrolo[2,3-c]pyridine-7-carbonitrile

Participants

Reaction Conditions

Reaction Steps

To a solution of 5-(2,6-diethyl-phenyl)-1-(1-propyl-butyl)-1H-pyrrolo[2,3-c]pyridine 6-oxide (220 mg, 0.6 mmol) in toluene (3 mL), is added dimethylsulfate (69 μL, 0.72 mmol), and the mixture is heated to 90° C. for 2 h. All volatiles are removed under reduced pressure. The residue is treated with water (2 mL), 10 M NaOH (20 drops) and KCN (200 mg, 3.1 mmol). The mixture is stirred for 12 h at room temperature. The product is extracted with EtOAc several times. The combined organic extracts are washed with brine, dried over Na2SO4, and concentrated under reduced pressure. Chromatography of the residue on silica gel (Hexane/EtOAc, 1:1) gives 5-(2,6-diethyl-phenyl)-1-(1-propyl-butyl)-1H-pyrrolo[2,3-c]pyridine-7-carbonitrile as a colorless oil: 1H NMR (CDCl3) 7.66 (s, 1H), 7.50 (d, J=3 Hz, 1H), 7.32 (t, J=7 Hz, 1H), 7.16 (d, J=7 Hz, 2H), 6.70 (d, J=3 Hz, 1H), 5.34 (m, 1H), 2.32 (m, 4H), 1.92 (m, 4H), 1.44 (m, 2H), 1.21 (m, 2H), 1.02 (t, J=7 Hz, 6H), 0.95 (t, J=7 Hz, 6H); LCMS m/z 374.27 (3.06 min).

Provenance & Evidence