Dichloromethane → HCID 67549384, compound

HRID 2356731Notes

Reaction equation

HRID 2356731 reaction equation
[C:1]([CH2:3][CH2:4][C:5]1[NH:9][C:8]([C:10]2[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=2)=[N:7][C:6]=1[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[O:23]C)#[N:2].B(Br)(Br)Br.C(=O)([O-])O.[Na+].[Cl:34]CCl>>[ClH:34].[C:1]([CH2:3][CH2:4][C:5]1[NH:9][C:8]([C:10]2[CH:11]=[CH:12][C:13]([F:16])=[CH:14][CH:15]=2)=[N:7][C:6]=1[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[OH:23])#[N:2]

Participants

5

Reactant 4

HCID 6344DichloromethaneHCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 59384876HCID 59384876, compound

Product 1

HCID 67549384HCID 67549384, compound

Procedure

To a solution of 5-(2-cyanoethyl)-2-(4-fluorophenyl)-4-(2-methoxyphenyl)imidazole (40 mg) in dichloromethane (10 ml) was added dropwise boron tribromide (94 mg) under ice-cooling, and the mixture was stirred at room temperature overnight. To the reaction mixture was added dropwise a saturated aqueous sodium hydrogen carbonate solution under ice-cooling, and then, the mixture was extracted with chloroform. The organic layer was dried over anhydrous sodium sulfate, and the solvent was removed under reduced pressure. The residue was purified by preparative TLC (solvent: hexane:ethyl acetate=1:1), and further purified by NH silica gel column chromatography (solvent: hexane:ethyl acetate=1:1). To the product was added hydrogen chloride-ethanol solution and the mixture was concentrated to obtain 5-(2-cyanoethyl)-2-(4-fluorophenyl)-4-(2-hydroxyphenyl)-imidazole hydrochloride (6 mg) as colorless solid.

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. extractionthe mixture was extracted with chloroform
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. customthe solvent was removed under reduced pressure
  6. customThe residue was purified by preparative TLC (solvent: hexane:ethyl acetate=1:1)
  7. customfurther purified by NH silica gel column chromatography (solvent: hexane:ethyl acetate=1:1)
  8. additionTo the product was added hydrogen chloride-ethanol solution
  9. concentrationthe mixture was concentrated

Sources & evidence

ORD record
ord-dd5496565e1d4b2a8eceba9598d1b93f
Source dataset
uspto-grants-2010_07
Patent number
US07759373B2

Reaction notes

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