1,1'-Carbonyldiimidazole → 2-Methyl-1-(6-phenylpyridin-3-yl)propyl 1H-imidazole-1-carboxylate

HRID 1054080Notes

Reaction equation

HRID 1054080 reaction equation
[CH3:1][CH:2]([CH3:17])[CH:3]([C:5]1[CH:6]=[N:7][C:8]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:9][CH:10]=1)[OH:4].[CH:18]1[N:22]=[CH:21][N:20]([C:23](N2C=NC=C2)=[O:24])[CH:19]=1>C(#N)C>[N:20]1([C:23]([O:4][CH:3]([C:5]2[CH:6]=[N:7][C:8]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)=[CH:9][CH:10]=2)[CH:2]([CH3:17])[CH3:1])=[O:24])[CH:19]=[CH:18][N:22]=[CH:21]1

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 675104242-Methyl-1-(6-phenylpyridin-3-yl)propan-1-ol

Product 1

HCID 573298692-Methyl-1-(6-phenylpyridin-3-yl)propyl 1H-imidazole-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Synthesized using compound 43a (81 mg, 0.36 mmol), CDI (289 mg, 1.78 mmol) and acetonitrile (5 mL) according to Method E. Crude product was purified by flash chromatography on silica-gel using a mixture of hexane/ethyl acetate (4:1) as eluent. White solid. Yield: 90.0 mg, 90%. 1H NMR (CDCl3, 500 MHz): δH (ppm)=0.95 (d, J=6.9 Hz, 3H), 1.14 (d, J=6.6 Hz, 3H), 2.37 (m, 1H), 5.70 (d, J=8.2 Hz, 1H), 7.09 (dd, J=1.6, 0.6 Hz, 1H), 7.40-7.51 (m, 4H), 7.72-7.79 (m, 2H), 7.98-8.03 (m, 2H), 8.19 (t, J=0.9 Hz, 1H), 8.71 (dd, J=2.2, 0.6 Hz, 1H); 13C NMR (CDCl3, 125 MHz): δC (ppm)=18.7, 18.8, 33.6, 83.7, 117.2, 120.4, 127.1, 129.0, 129.5, 131.1, 131.8, 135.6, 137.2, 138.8, 148.7, 158.0; MS (ESI): m/z=322.32 [M+H]+.

Workup

  1. customSynthesized
  2. customCrude product was purified by flash chromatography on silica-gel
  3. additiona mixture of hexane/ethyl acetate (4:1) as eluent

Sources & evidence

ORD record
ord-2aa067969fb74bc88e9aaaa3bbdb9864
Source dataset
uspto-grants-2016_07
Patent number
US09394290B2

Reaction notes

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