Dichloromethane → HCID 15129906, compound

HRID 1681374Notes

Reaction equation

HRID 1681374 reaction equation
[CH2:1]([C:5]1[NH:6][C:7]2[CH:13]=[CH:12][CH:11]=[CH:10][C:8]=2[N:9]=1)[CH2:2][CH2:3][CH3:4].Br[CH2:15][C:16]1[CH:21]=[CH:20][C:19]([C:22]2[C:23]([C:28]([O:30][CH3:31])=[O:29])=[CH:24][CH:25]=[CH:26][CH:27]=2)=[CH:18][CH:17]=1.C(=O)([O-])[O-].[K+].[K+].ClCCl>CN(C)C=O>[CH2:1]([C:5]1[N:6]([CH2:15][C:16]2[CH:21]=[CH:20][C:19]([C:22]3[C:23]([C:28]([O:30][CH3:31])=[O:29])=[CH:24][CH:25]=[CH:26][CH:27]=3)=[CH:18][CH:17]=2)[C:7]2[CH:13]=[CH:12][CH:11]=[CH:10][C:8]=2[N:9]=1)[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 11430Potassium CarbonateHCID 22122Benzimidazole, 2-butyl-HCID 11012181Methyl 4'-(bromomethyl)biphenyl-2-carboxylate

Product 1

HCID 15129906HCID 15129906, compoundYield 45.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-butylbenzimidazole (2.6 g), the bromomethyl compound (C) (5.0 g) and potassium carbonate (1.55 g) in N,N-dimethylformamide (DMF) (40 ml) was heated at 100° C. for 3 hours. Dichloromethane (200 ml) was added and insoluble material was removed by filtration. The filtrate was concentrated and the residue purified by flash chromatography, eluting with triethylamine/ethyl acetate/hexane (1:40:60 v/v), to give methyl 4'-[2-butyl-1H-benzimidazol-1-yl)methyl]biphenyl-2-carboxylate (A) as a clear oil (2.7 g); NMR (CDCl3): 0.95(t,3H), 1.45(m,2H), 2.9(t,2H), 3.6(s,3H), 5.4(s,2H), 7.2(d,2H), 7.2-7.6 (complex m,3H), 7.8(m,2H).

Workup

  1. custominsoluble material was removed by filtration
  2. concentrationThe filtrate was concentrated
  3. customthe residue purified by flash chromatography
  4. washeluting with triethylamine/ethyl acetate/hexane (1:40:60 v/v)

Sources & evidence

ORD record
ord-35314c8c8c59467eaf1aaad9324e652d
Source dataset
uspto-grants-1992_12
Patent number
US05171748

Reaction notes

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