Imidazo[1,2-a]pyrimidine, 3-(tributylstannyl)-7-(trifluoromethyl)- → 3-[2'-([1,2,4]Triazol-1-yl)biphenyl-3-yl]-7-trifluoromethylimidazo[1,2-a]pyrimidine

HRID 478252Notes

Reaction equation

HRID 478252 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[N:14]2[CH:18]=[N:17][CH:16]=[N:15]2)[CH:5]=[CH:6][CH:7]=1.C([Sn](CCCC)(CCCC)[C:24]1[N:28]2[CH:29]=[CH:30][C:31]([C:33]([F:36])([F:35])[F:34])=[N:32][C:27]2=[N:26][CH:25]=1)CCC>CO.ClCCl>[N:14]1([C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([C:24]3[N:28]4[CH:29]=[CH:30][C:31]([C:33]([F:34])([F:35])[F:36])=[N:32][C:27]4=[N:26][CH:25]=3)[CH:3]=2)[CH:18]=[N:17][CH:16]=[N:15]1

Participants

5

Reactant 2

HCID 11294484Imidazo[1,2-a]pyrimidine, 3-(tributylstannyl)-7-(trifluoromethyl)-HCID 180012791-(3'-bromobiphenyl-2-yl)-1H-[1,2,4]triazole

Product 1

HCID 101794683-[2'-([1,2,4]Triazol-1-yl)biphenyl-3-yl]-7-trifluoromethylimidazo[1,2-a]pyrimidine

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

1-(3′-Bromobiphenyl-2-yl)-1H-[1,2,4]triazole (91 mg, 0.30 mmol) was coupled to 3-tributylstannyl-7-trifluoromethylimidazo[1,2-a]pyrimidine (0.25 mmol) by the method of Example 32. The product was obtained by preparative thin-layer chromatography on silica gel with 3% methanol in dichloromethane as eluent followed by high performance liquid chromatography to give 3-[2′-([1,2,4]triazol-1-yl)biphenyl-3-yl]-7-trifluoromethylimidazo[1,2-a]pyrimidine as a yellow solid: δH (400 MHz, CDCl3) 8.57 (1H, d, J 7), 7.95-8.11 (3H, m), 7.48-7.66 (7H, m), 7.35 (1H, J 8), 7.27 (1H, m); m/z (ES+) 407 (M++H).

Sources & evidence

ORD record
ord-afe692c0c5d5474c8490b62b0f7422a0
Source dataset
uspto-grants-2003_11
Patent number
US06642229B2

Reaction notes

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