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

HRID 1500399노트

반응식

HRID 1500399 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-95c78ed372164227b9144b6643cc8019
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09206164B2

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