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Cesium carbonate → (E)-4-methyl-2-(prop-1-enyl)-7-(trifluoromethyl)quinoline-3-carboxylic acid ethyl ester

HRID 2093721
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HRID 2093721 반응식
C([O-])([O-])=O.[Cs+].[Cs+].[CH2:7]([O:9][C:10]([C:12]1[C:13](OS(C(F)(F)F)(=O)=O)=[N:14][C:15]2[C:20]([C:21]=1[CH3:22])=[CH:19][CH:18]=[C:17]([C:23]([F:26])([F:25])[F:24])[CH:16]=2)=[O:11])[CH3:8].[CH:35](/B(O)O)=[CH:36]\[CH3:37].C(O)C.C1(C)C=CC=CC=1>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CC(=O)OCC.CCCCCC>[CH2:7]([O:9][C:10]([C:12]1[C:13](/[CH:35]=[CH:36]/[CH3:37])=[N:14][C:15]2[C:20]([C:21]=1[CH3:22])=[CH:19][CH:18]=[C:17]([C:23]([F:26])([F:25])[F:24])[CH:16]=2)=[O:11])[CH3:8]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 10796Cesium carbonateHCID 6157276((1E)-prop-1-en-1-yl)boronic acidHCID 21863594Toluene ethanolHCID 866626824-Methyl-7-(trifluoromethyl)-2-(trifluoromethylsulfonyl-oxy)quinoline-3-carboxylic acid ethyl ester

생성물 1

HCID 66583793(E)-4-methyl-2-(prop-1-enyl)-7-(trifluoromethyl)quinoline-3-carboxylic acid ethyl ester수율 75%

시약·촉매·용매

2
HCID 178418397HCID 178418397, 화합물촉매HCID 21226206Ethyl acetate hexane용매

반응 조건

온도
110 °C

실험 절차

1.8 g (5.6 mmol) Cs2CO3 and 210 mg (0.2 mmol) Pd(PPh3)4 were added to a solution of 800 mg (1.9 mmol) 4-methyl-7-(trifluoromethyl)-2-(trifluoromethyl-sulfonyloxy)-quinoline-3-carboxylic acid ethyl ester and 320 mg (3.7 mmol) (E)-propene-1-yl-boronic acid in an ethanol/toluene mixture (1:9 vv, 20 ml) and the mixture was heated to 110° C. for 1 h. The mixture was thereafter concentrated in a vacuum and the residue was taken up with EtOAc (20 ml) and water (20 ml). The organic phase was separated, washed with water and brine, dried over Na2SO4 and concentrated in a vacuum. After CC (EA/hexane 1:9) of the residue, 450 mg (1.4 mmol, 75%) (E)-4-methyl-2-(prop-1-enyl)-7-(trifluoromethyl)quinoline-3-carboxylic acid ethyl ester was obtained.

후처리

  1. concentrationThe mixture was thereafter concentrated in a vacuum
  2. customThe organic phase was separated
  3. washwashed with water and brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in a vacuum

출처 및 근거

ORD 기록
ord-ee15b7fba11342268d805fee9a0e843e
출처 데이터셋
uspto-grants-2013_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08445512B2

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