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Cesium carbonate → Isopropyl 2-[3-[[5-(3,5-difluorophenyl)-2,3-dimethyl-phenyl]methylamino]-2,4-difluoro-phenoxy]acetate

HRID 1771825
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HRID 1771825 반응식
[F:1][C:2]1[CH:3]=[C:4]([C:9]2[CH:10]=[C:11]([CH3:27])[C:12]([CH3:26])=[C:13]([CH2:15][NH:16][C:17]3[C:18]([F:25])=[C:19]([OH:24])[CH:20]=[CH:21][C:22]=3[F:23])[CH:14]=2)[CH:5]=[C:6]([F:8])[CH:7]=1.C([O-])([O-])=O.[Cs+].[Cs+].Br[CH2:35][C:36]([O:38][CH:39]([CH3:41])[CH3:40])=[O:37]>CN(C=O)C.O>[F:1][C:2]1[CH:3]=[C:4]([C:9]2[CH:10]=[C:11]([CH3:27])[C:12]([CH3:26])=[C:13]([CH2:15][NH:16][C:17]3[C:18]([F:25])=[C:19]([CH:20]=[CH:21][C:22]=3[F:23])[O:24][CH2:35][C:36]([O:38][CH:39]([CH3:41])[CH3:40])=[O:37])[CH:14]=2)[CH:5]=[C:6]([F:8])[CH:7]=1
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참가 물질

6

반응물 3

HCID 10796Cesium carbonateHCID 121593Isopropyl bromoacetateHCID 894437053-[[5-(3,5-Difluorophenyl)-2,3-dimethyl-phenyl]methylamino]-2,4-difluoro-phenol

생성물 1

HCID 89445489Isopropyl 2-[3-[[5-(3,5-difluorophenyl)-2,3-dimethyl-phenyl]methylamino]-2,4-difluoro-phenoxy]acetate수율 96.7%

시약·촉매·용매 2

HCID 962Water
용매
HCID 6228Dimethylformamide용매

실험 절차

To a solution of 3-[[5-(3,5-difluorophenyl)-2,3-dimethyl-phenyl]methylamino]-2,4-difluoro-phenol (20 mg, 0.05 mmol, 1.0 eq) in DMF (3 mL) was added Cs2CO3 (26 mg, 0.075 mmol, 1.5 eq). The mixture was stirred at room temperature for 30 min then isopropyl bromoacetate (11 mg, 0.06 mmol, 1.2 eq) was added. The reaction mixture was stirred at room temperature for a further 1 h then diluted with water and extracted with EtOAc. The combined organic extracts were washed with water and brine, dried (Na2SO4), filtered and evaporated in vacuo. The residue was purified by column chromatography (petroleum ether:EtOAc, 30:1) to give the title compound as a colorless oil (23 mg, 92%).

후처리

  1. stirringThe reaction mixture was stirred at room temperature for a further 1 h
  2. extractionextracted with EtOAc
  3. washThe combined organic extracts were washed with water and brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customThe residue was purified by column chromatography (petroleum ether:EtOAc, 30:1)

출처 및 근거

ORD 기록
ord-033f2d46289c4bea890211ba8791080c
출처 데이터셋
uspto-grants-2016_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09249085B2

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