Water → HCID 67546932, 화합물

HRID 2096795노트

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HRID 2096795 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

HCID 67546932HCID 67546932, 화합물수율 47.4%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

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+].

후처리

  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)

출처 및 근거

ORD 기록
ord-5c4a1cb1501541c292126b1910582d38
출처 데이터셋
uspto-grants-2013_05
특허 번호
US08450313B2

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