Water → HCID 19955574, compound

HRID 1779446Notes

Reaction equation

HRID 1779446 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[I:15])=[CH:5][CH:4]=1.[CH2:16]([C:20]1[NH:21][C:22]([CH:26]=[O:27])=[C:23]([Cl:25])[N:24]=1)[CH2:17][CH2:18][CH3:19].C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[CH2:16]([C:20]1[N:21]([CH2:2][C:3]2[CH:8]=[CH:7][C:6]([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[I:15])=[CH:5][CH:4]=2)[C:22]([CH:26]=[O:27])=[C:23]([Cl:25])[N:24]=1)[CH2:17][CH2:18][CH3:19]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 19955577HCID 19955577, compoundHCID 178418251HCID 178418251, compound

Product 1

HCID 19955574HCID 19955574, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of 4-(bromomethyl)-2'-iodobiphenyl (9.23 g; preparable as described in Example 2(b)) in dry dimethylformamide (50 ml) was added to a stirring mixture of 2-butyl-4-chloro-1H-imidazole-5-carboxaldehyde (preparable as described in Drugs of the Future (1991), Vol. 16, p 305), anhydrous potassium carbonate (6.9 g) and dry dimethylformamide (100 ml), at ambient temperature. Stirring was continued at ambient temperature for 24 hours. Water (200 ml) was added and the resulting mixture was extracted with diethyl ether (500 ml then 200 ml). The combined extracts were washed with water (2×100 ml) and dried over magnesium sulphate. The organic solvent was evaporated and the residual orange oil was purified by flash chromatography on silica gel (eluting with 5% then 30% ethyl acetate in petroleum ether (b.p. 60°-80° C.)) to give the intermediate compound 2-butyl-4-chloro-1-(2'-iodobiphenyl-4-ylmethyl)-1H-imidazol-5-carboxaldehyde as a yellow oil (8.06 g).

Workup

  1. customat ambient temperature
  2. extractionthe resulting mixture was extracted with diethyl ether (500 ml
  3. washThe combined extracts were washed with water (2×100 ml)
  4. dry with materialdried over magnesium sulphate
  5. customThe organic solvent was evaporated
  6. customthe residual orange oil was purified by flash chromatography on silica gel (
  7. washeluting with 5%

Sources & evidence

ORD record
ord-b7fd847731ba4460a8cb8a274e261b08
Source dataset
uspto-grants-1997_05
Patent number
US05627191

Reaction notes

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