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

HRID 1163090ノート

反応式

HRID 1163090 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
100 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-5fb8cc03dd4f43a7975b149e513880c5
出典データセット
uspto-grants-2010_10
特許番号
US07820825B2

反応ノート

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