Water → tert-butyl 2-(1-(4-iodobenzyl)-3,5-dimethyl-1H-pyrazol-4-yl)acetate

HRID 1500399ノート

反応式

HRID 1500399 の反応式
[C:1]([O:5][C:6](=[O:15])[CH2:7][C:8]1[C:9]([CH3:14])=[N:10][NH:11][C:12]=1[CH3:13])([CH3:4])([CH3:3])[CH3:2].Br[CH2:17][C:18]1[CH:23]=[CH:22][C:21]([I:24])=[CH:20][CH:19]=1.C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[C:1]([O:5][C:6](=[O:15])[CH2:7][C:8]1[C:12]([CH3:13])=[N:11][N:10]([CH2:17][C:18]2[CH:23]=[CH:22][C:21]([I:24])=[CH:20][CH:19]=2)[C:9]=1[CH3:14])([CH3:4])([CH3:3])[CH3:2]

参加物

6

反応物 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 9542584-Iodobenzyl bromideHCID 66707418tert-butyl 2-(3,5-dimethyl-1H-pyrazol-4-yl)acetate

生成物 1

HCID 68390870tert-butyl 2-(1-(4-iodobenzyl)-3,5-dimethyl-1H-pyrazol-4-yl)acetate収率 60.2%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a stirred solution of (3,5-dimethyl-1H-pyrazol-4-yl)acetic acid tert.-butyl ester (10 g) in dimethylformamid (50 ml) at room temperature is added 1-bromomethyl-4-iodobenzene (15.5 g) and potassium carbonate (8.0 g). After 15 h of stirring, water is added and the reaction mixture is extracted twice with ethyl acetate. The organic layer is washed several times with water, dried over magnesium sulfate and concentrated in vacuo. The residue is purified by flash chromatography (4:1 to 3:2 cyclohexane:ethyl acetate) to yield 1-(4-iodobenzyl)-3,5-dimethyl-1H-pyrazol-4-yl-acetic acid tert.-butyl ester (12.2 g). [M+H]=427; HPLC retention time 1.57 min (Method E).

後処理

  1. extractionthe reaction mixture is extracted twice with ethyl acetate
  2. washThe organic layer is washed several times with water
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue is purified by flash chromatography (4:1 to 3:2 cyclohexane:ethyl acetate)

出典と根拠

ORDレコード
ord-95c78ed372164227b9144b6643cc8019
出典データセット
uspto-grants-2015_12
特許番号
US09206164B2

反応ノート

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