2-Methylbenzonitrile → [4-(5-Ethyl-3-pyridin-3-yl-pyrazol-1-yl)phenyl]-(2-methylbenzyl)amine

反応式

[CH2:1]([C:3]1[N:7]([C:8]2[CH:13]=[CH:12][C:11]([NH2:14])=[CH:10][CH:9]=2)[N:6]=[C:5]([C:15]2[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=2)[CH:4]=1)[CH3:2].[C:21]1([CH3:29])[C:22]([C:27]#N)=[CH:23][CH:24]=[CH:25][CH:26]=1>C(O)(=O)C.[Ni]>[CH2:1]([C:3]1[N:7]([C:8]2[CH:9]=[CH:10][C:11]([NH:14][CH2:29][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[CH3:27])=[CH:12][CH:13]=2)[N:6]=[C:5]([C:15]2[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=2)[CH:4]=1)[CH3:2]

参加物

実験手順

A slurry of Raney Ni (200 mg, 50% in water) was added to a solution 5-ethyl-3-(3-pyridyl)-1-(4′-aminophenyl)pyrazole (500 mg, 1.89 mmol) and o-tolunitrile (0.27 mL, 1.2 equiv.) in glacial acetic acid (20 mL), and the mixture was stirred under hydrogen at 40 psi for 7.5 h. The reaction mixture was filtered through diatomaceous earth, diluted with water, extracted with ethyl acetate, washed with brine, dried (Na2SO4) and concentrated. Chromatography on silica gel (hexane/ethyl acetate=1:1) gave the title compound (595 mg, 85%). 1H-NMR (CDCl3): 1.30 (t, J=7.5 Hz, 3H), 2.42 (s, 3H), 2.69 (q, J=7.5 Hz, 2H), 3.95-4.25 (bs, 1H), 4.36 (s, 2H), 6.58 (s, 1H), 6.72 (d, J=8.7 Hz, 1H), 7.21-7.41 (m, 6H), 8.21 (dd, J=1.6, 6.3 Hz, 1H), 8.56 (d, J=4.1 Hz, 1H), 9.10 (d, J=1.6 Hz, 1H).