Water → HCID 67546932, compound

HRID 2386784Notes

Reaction equation

HRID 2386784 reaction equation
[Li]CCCC.Br[C:7]1[CH:18]=[CH:17][C:10]2[N:11]([CH3:16])[C:12](=[O:15])[N:13]([CH3:14])[C:9]=2[CH:8]=1.[Br:19][C:20]1[CH:25]=[CH:24][C:23]([CH:26]([CH3:29])[CH:27]=[O:28])=[C:22]([Cl:30])[CH:21]=1.O>C1COCC1>[Br:19][C:20]1[CH:25]=[CH:24][C:23]([CH:26]([CH3:29])[CH:27]([C:7]2[CH:18]=[CH:17][C:10]3[N:11]([CH3:16])[C:12](=[O:15])[N:13]([CH3:14])[C:9]=3[CH:8]=2)[OH:28])=[C:22]([Cl:30])[CH:21]=1

Participants

6

Reactant 4

HCID 962WaterHCID 470034475-Bromo-1,3-dihydro-1,3-dimethyl-2H-benzimidazol-2-oneHCID 82780306HCID 82780306, compoundHCID 178418339Butyllithium

Product 1

HCID 67546932HCID 67546932, compoundYield 47.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A 1.6M solution of n-BuLi in hexanes (0.62 ml) was added at −78° C. to a solution of 5-bromo-1,3-dimethyl-1,3-dihydro-benzoimidazol-2-one (241 mg) in THF at (10 ml). The gray suspension was stirred for 10 min, then a solution of 2-(4-bromo-2-chloro-phenyl)-propionaldehyde (248 mg) in THF (2 ml) was added. The mixture was stirred for 10 min at −78° C. and then warmed to room temperature. Water (25 ml) was added and extracted with DCM. The combined organic layers were dried over Na2SO4 and concentrated to an oil. The residue was purified by flash chromatography (SiO2, 0 to 100% EtOAc/heptane) to give the title compound (194 mg) as a colorless oil. MS (m/e)=409.1 [M+H+].

Workup

  1. stirringThe mixture was stirred for 10 min at −78° C.
  2. extractionextracted with DCM
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. concentrationconcentrated to an oil
  5. customThe residue was purified by flash chromatography (SiO2, 0 to 100% EtOAc/heptane)

Sources & evidence

ORD record
ord-4edce06029cc4f118f54f9fc5ef8870a
Source dataset
uspto-grants-2012_09
Patent number
US08268820B2

Reaction notes

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