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Cesium carbonate → [4-({3-[3-Methyl-8-(Trifluoromethyl)Quinolin-4-yl]Phenoxy}Methyl)Phenyl]Acetic Acid

HRID 2104602
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인쇄 미리보기

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HRID 2104602 반응식
[CH3:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([C:11]=1[C:12]1[CH:13]=[C:14]([OH:18])[CH:15]=[CH:16][CH:17]=1)=[CH:9][CH:8]=[CH:7][C:6]=2[C:19]([F:22])([F:21])[F:20].Br[CH2:24][C:25]1[CH:30]=[CH:29][C:28]([CH2:31][C:32]([OH:34])=[O:33])=[CH:27][CH:26]=1.C([O-])([O-])=O.[Cs+].[Cs+]>C(Cl)Cl>[CH3:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([C:11]=1[C:12]1[CH:13]=[C:14]([CH:15]=[CH:16][CH:17]=1)[O:18][CH2:24][C:25]1[CH:26]=[CH:27][C:28]([CH2:31][C:32]([OH:34])=[O:33])=[CH:29][CH:30]=1)=[CH:9][CH:8]=[CH:7][C:6]=2[C:19]([F:22])([F:20])[F:21]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 10796Cesium carbonateHCID 45190564-(Bromomethyl)phenylacetic acidHCID 665862653-[3-Methyl-8-(trifluoromethyl)quinolin-4-yl]phenol

생성물 1

HCID 16718749[4-({3-[3-Methyl-8-(Trifluoromethyl)Quinolin-4-yl]Phenoxy}Methyl)Phenyl]Acetic Acid

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
70 °C

실험 절차

3-[3-Methyl-8-(trifluoromethyl)quinolin-4-yl]phenol (1.13 g, 3.73 mmol) and 4-bromomethylphenylacetic acid (1.02 g, 4.47 mmol) in CH2Cl2 (60 mL) is treated with Cs2CO3 (4.86 g, 14.9 mmol) and the reaction is stirred overnight. The solvent is removed and the residue dissolved in THF and 2N aq NaOH. After heating at 70° C. for 1 h, the reaction is cooled and the layers separated. The aqueous layer is further extracted with ethyl acetate. The combined organics are dried (Na2SO4) and concentrated. The residue is chromatographed eluting with 20:80 ethyl acetate:hexane and then 5:95 methanol:methylene chloride to afford the title product.

후처리

  1. customThe solvent is removed
  2. dissolutionthe residue dissolved in THF
  3. temperaturethe reaction is cooled
  4. customthe layers separated
  5. extractionThe aqueous layer is further extracted with ethyl acetate
  6. dry with materialThe combined organics are dried (Na2SO4)
  7. concentrationconcentrated
  8. customThe residue is chromatographed
  9. washeluting with 20:80 ethyl acetate

출처 및 근거

ORD 기록
ord-b5d2507d4be84c6eb619f3d095950bc2
출처 데이터셋
uspto-grants-2009_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07576215B2

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