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Sodium Carbonate → Ethyl 3-cyclopropyl-3-(3-(((2-fluoro-5-methoxy-4''-(trifluoromethyl)-1,1':2',1''-terphenyl-4'-yl)oxy)methyl)phenyl)propanoate

HRID 1049452
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HRID 1049452 반응식
[CH:1]1([CH:4]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([CH2:17][O:18][C:19]3[CH:24]=[CH:23][C:22]([C:25]4[CH:30]=[C:29]([O:31][CH3:32])[CH:28]=[CH:27][C:26]=4[F:33])=[C:21](OS(C(F)(F)F)(=O)=O)[CH:20]=3)[CH:12]=2)[CH2:5][C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH2:3][CH2:2]1.[F:42][C:43]([F:54])([F:53])[C:44]1[CH:49]=[CH:48][C:47](B(O)O)=[CH:46][CH:45]=1.C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH:1]1([CH:4]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([CH2:17][O:18][C:19]3[CH:20]=[C:21]([C:47]4[CH:48]=[CH:49][C:44]([C:43]([F:54])([F:53])[F:42])=[CH:45][CH:46]=4)[C:22]([C:25]4[CH:30]=[C:29]([O:31][CH3:32])[CH:28]=[CH:27][C:26]=4[F:33])=[CH:23][CH:24]=3)[CH:12]=2)[CH2:5][C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH2:3][CH2:2]1
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참가 물질

7

반응물 4

HCID 10340Sodium CarbonateHCID 27343894-(Trifluoromethyl)phenylboronic acidHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 117759787Ethyl 3-cyclopropyl-3-(3-(((2'-fluoro-5'-methoxy-2-(((trifluoromethyl)sulfonyl)oxy)biphenyl-4-yl)oxy)methyl)phenyl)propanoate

생성물 1

HCID 117760114
Ethyl 3-cyclopropyl-3-(3-(((2-fluoro-5-methoxy-4''-(trifluoromethyl)-1,1':2',1''-terphenyl-4'-yl)oxy)methyl)phenyl)propanoate
수율 56.4%

시약·촉매·용매 2

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 1140Toluene용매

반응 조건

온도
90 °C

실험 절차

Under a nitrogen atmosphere, to a solution of ethyl 3-cyclopropyl-3-(3-(((2′-fluoro-5′-methoxy-2-(((trifluoromethyl)sulfonyl)oxy)biphenyl-4-yl)oxy)methyl)phenyl)propanoate (173 mg) in toluene (5.0 mL) were added 4-(trifluoromethyl)phenylboronic acid (157 mg), tris(dibenzylideneacetone)dipalladium(0) (20 mg), 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (39 mg) and 2.0 M aqueous sodium carbonate solution (0.43 mL), and the mixture was stirred at 90° C. for 15 hr. The reaction mixture was filtered through celite, water was added to the filtrate, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (97 mg) as a colorless oil.

후처리

  1. filtrationThe reaction mixture was filtered through celite, water
  2. additionwas added to the filtrate
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

출처 및 근거

ORD 기록
ord-2a75403eef344e93b7c310d0027d122c
출처 데이터셋
uspto-grants-2016_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09382188B2

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