1-(3-bromophenyl)-1H-imidazole → 3-[3-(Imidazol-1-yl)phenyl]-7-trifluoromethylimidazo[1,2-a]pyrimidine

HRID 478247Notes

Reaction equation

HRID 478247 reaction equation
C([Sn](CCCC)(CCCC)[C:6]1[N:10]2[CH:11]=[CH:12][C:13]([C:15]([F:18])([F:17])[F:16])=[N:14][C:9]2=[N:8][CH:7]=1)CCC.Br[C:28]1[CH:29]=[C:30]([N:34]2[CH:38]=[CH:37][N:36]=[CH:35]2)[CH:31]=[CH:32][CH:33]=1>[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[N:34]1([C:30]2[CH:29]=[C:28]([C:6]3[N:10]4[CH:11]=[CH:12][C:13]([C:15]([F:16])([F:17])[F:18])=[N:14][C:9]4=[N:8][CH:7]=3)[CH:33]=[CH:32][CH:31]=2)[CH:38]=[CH:37][N:36]=[CH:35]1

Participants

4

Reactant 2

HCID 3120961-(3-bromophenyl)-1H-imidazoleHCID 11294484Imidazo[1,2-a]pyrimidine, 3-(tributylstannyl)-7-(trifluoromethyl)-

Product 1

HCID 99235143-[3-(Imidazol-1-yl)phenyl]-7-trifluoromethylimidazo[1,2-a]pyrimidineYield 21.3%

Reagents, catalysts & solvents 1

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalyst

Procedure

To a degassed solution of 3-tributylstannyl-7-trifluoromethyl-imidazo[1,2-a]pyrimidine (1.4 mmol) was added 1-(3-bromophenyl)-1H-imidazole (0.60 g, 2.7 mmol) (prepared by the method of A. Johnson et al., J. Med. Chem., 1969, 12(5), 1024-8) and tetrakis(triphenylphosphine)-palladium(0) (218 mg, 0.18 mmol) and the mixture heated at reflux for 18 h. The crude reaction was adsorbed onto silica and chromatographed on silica, eluting on a gradient of 1 to 5% methanol in dichloromethane, to give a yellow oil. Crystallisation from ethyl acetatelisohexane afforded 3-[3-(imidazol-1-yl)phenyl]-7-trifluoromethylimidazo[1,2-a]pyrimidine (0.098 g) as a white solid: δH (400 MHz; DMSO) 7.15 (1H, s), 7.53 (1H, d, J 7.4), 7.73 (1H, dd, J 3.1 and 1.6), 7.74 (1H, d, J 0.8), 7.78-7.81 (1H, m), 7.89 (1H, t, J 1.4), 8.08 (1H, dd, J 1.6 and 1.2), 8.39 (2H, d, J 7.0), 9.44 (1H, d, J 6.7); m/z (ES+) 330 (M++H).

Workup

  1. customprepared by the method of A
  2. temperatureat reflux for 18 h
  3. customThe crude reaction
  4. customchromatographed on silica
  5. washeluting on a gradient of 1 to 5% methanol in dichloromethane
  6. customto give a yellow oil
  7. customCrystallisation from ethyl acetatelisohexane

Sources & evidence

ORD record
ord-6769a4ce40bc432b92b7c5d5d3bd5e7a
Source dataset
uspto-grants-2003_11
Patent number
US06642229B2

Reaction notes

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