1,1'-Carbonyldiimidazole → 1-(6-phenylpyridin-3-yl)ethyl 1H-imidazole-1-carboxylate
Reaction equation
[C:1]1([C:7]2[N:12]=[CH:11][C:10]([CH:13]([OH:15])[CH3:14])=[CH:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH:16]1[N:20]=[CH:19][N:18]([C:21](N2C=NC=C2)=[O:22])[CH:17]=1>C(#N)C>[N:18]1([C:21]([O:15][CH:13]([C:10]2[CH:11]=[N:12][C:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)=[CH:8][CH:9]=2)[CH3:14])=[O:22])[CH:17]=[CH:16][N:20]=[CH:19]1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
Synthesized using compound 45a (170 mg, 0.85 mmol), CDI (692 mg, 4.27 mmol) and acetonitrile (10 mL) according to Method E. Crude product was purified by flash chromatography on silica-gel using a mixture of hexane/ethyl acetate (2:1) as eluent. White solid. Yield: 107 mg, 43%. 1H NMR (CDCl3, 500 MHz): δH (ppm)=1.82 (d, J=6.9 Hz, 3H), 6.16 (q, J=6.6 Hz, 1H), 7.08 (dd, J=1.7, 0.8 Hz, 1H), 7.41-7.53 (m, 4H), 7.76-7.85 (m, 2H), 7.98-8.03 (m, 2H), 8.17 (d, J=1.3 Hz, 1H), 8.78 (d, J=1.9 Hz, 1H); 13C NMR (CDCl3, 125 MHz): δC (ppm)=21.5, 74.9, 117.1, 120.4, 126.9, 128.8, 129.3, 130.8, 133.3, 134.7, 137.0, 138.6, 147.9, 148.0, 158.0; MS (ESI): m/z=294.28 [M+H]+.