Phenethyl bromide → 4-(1-phenethyl-1H-benzoimidazol-2-ylmethyl)-benzoic acid methyl ester

HRID 1163090노트

반응식

HRID 1163090 반응식
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[CH2:10][C:11]1[CH:20]=[CH:19][C:14]([C:15]([O:17][CH3:18])=[O:16])=[CH:13][CH:12]=1.Br[CH2:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH3:18][O:17][C:15](=[O:16])[C:14]1[CH:19]=[CH:20][C:11]([CH2:10][C:2]2[N:3]([CH2:22][CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[C:4]3[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=3[N:1]=2)=[CH:12][CH:13]=1

참가 물질

5

반응물 3

HCID 7666Phenethyl bromideHCID 11430Potassium CarbonateHCID 59468704methyl 4-((1H-benzo[d]imidazol-2-yl)methyl)benzoate

생성물 1

HCID 589707834-(1-phenethyl-1H-benzoimidazol-2-ylmethyl)-benzoic acid methyl ester수율 30%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

반응 조건

온도
100 °C

실험 절차

A solution of methyl 4-((1H-benzo[d]imidazol-2-yl)methyl)benzoate (200 mg, 0.75 mmol) in acetonitrile was treated with (2-bromoethyl)benzene (209 mg, 1.13 mmol) and potassium carbonate (143 mg, 0.90 mmol). The reaction mixture was heated with microwave irradiation at 100° C. for 2 h. The solvent was removed under reduced pressure and the residue was partitioned between water and dichloromethane. The organic phase was separated, dried over sodium sulfate and concentrated in vacuo. Purification of the resultant residue by flash column chromatography (silica, petroleum ether:ethyl acetate 8:2 to 1:1) afforded 4-(1-phenethyl-1H-benzoimidazol-2-ylmethyl)-benzoic acid methyl ester (30%). [M+H] 371.2.

후처리

  1. customThe solvent was removed under reduced pressure
  2. customthe residue was partitioned between water and dichloromethane
  3. customThe organic phase was separated
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customPurification of the resultant residue by flash column chromatography (silica, petroleum ether:ethyl acetate 8:2 to 1:1)

출처 및 근거

ORD 기록
ord-5fb8cc03dd4f43a7975b149e513880c5
출처 데이터셋
uspto-grants-2010_10
특허 번호
US07820825B2

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