Water → HCID 67546932、化合物

HRID 2096795ノート

反応式

HRID 2096795 の反応式
[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

参加物

6

反応物 4

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

生成物 1

HCID 67546932HCID 67546932、化合物収率 47.4%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

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+].

後処理

  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)

出典と根拠

ORDレコード
ord-5c4a1cb1501541c292126b1910582d38
出典データセット
uspto-grants-2013_05
特許番号
US08450313B2

反応ノート

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