1,1'-Carbonyldiimidazole → 1-(6-phenylpyridin-3-yl)propyl 1H-imidazole-1-carboxylate

HRID 1054082Notes

Reaction equation

HRID 1054082 reaction equation
[C:1]1([C:7]2[N:12]=[CH:11][C:10]([CH:13]([OH:16])[CH2:14][CH3:15])=[CH:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH:17]1[N:21]=[CH:20][N:19]([C:22](N2C=NC=C2)=[O:23])[CH:18]=1>C(#N)C>[N:19]1([C:22]([O:16][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)[CH2:14][CH3:15])=[O:23])[CH:18]=[CH:17][N:21]=[CH:20]1

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 675111421-(6-Phenylpyridin-3-yl)propan-1-ol

Product 1

HCID 573298701-(6-phenylpyridin-3-yl)propyl 1H-imidazole-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Synthesized using compound 44a (150 mg, 0.70 mmol), CDI (570 mg, 3.52 mmol) and acetonitrile (9 mL) according to Method E. Crude product was purified by flash chromatography on silica-gel using a mixture of hexane/ethyl acetate (3:1) as eluent. White solid. Yield: 116 mg, 54%. 1H NMR (CDCl3, 500 MHz): δH (ppm)=1.04 (t, J=7.4 Hz, 3H), 2.01-2.15 (m, 1H), 2.22 (dt, J=14.3, 7.2 Hz, 1H), 5.92 (t, J=7.1 Hz, 1H), 7.09 (dd, J=1.6, 0.6 Hz, 1H), 7.41-7.51 (m, 4H), 7.75-7.80 (m, 2H), 7.98-8.03 (m, 2H), 8.17-8.19 (m, 1H), 8.74-8.77 (m, 1H); 13C NMR (CDCl3, 125 MHz): δC (ppm)=9.8, 28.7, 79.8, 117.0, 120.3, 126.9, 128.8, 129.3, 130.8, 132.3, 135.0, 137.0, 138.6, 148.0, 148.3, 158.0; MS (ESI): m/z=308.30 [M+H]+.

Workup

  1. customSynthesized
  2. customCrude product was purified by flash chromatography on silica-gel
  3. additiona mixture of hexane/ethyl acetate (3:1) as eluent

Sources & evidence

ORD record
ord-28133a8172824305b8abcf4c9a35fe46
Source dataset
uspto-grants-2016_07
Patent number
US09394290B2

Reaction notes

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