Dimethylformamide → Methyl 5'-chloro-2-(5,5-dimethyl-1-cyclopenten-1-yl)-2'-fluoro-1,1'-biphenyl-4-carboxylate

HRID 1662517노트

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HRID 1662517 반응식
C1([C@H](C2C=CC=C(OC[C:17]3[CH:22]=[CH:21][C:20]([C:23]4[CH:28]=[C:27](OC)[CH:26]=[CH:25][C:24]=4F)=[C:19]([C@H:32](O)C(C)(C)C=C)[CH:18]=3)C=2)CC(O)=O)CC1.[Cl:39][C:40]1[CH:41]=[CH:42][C:43]([F:49])=[C:44](B(O)O)[CH:45]=1.[C:50](=[O:53])([O-])[O-:51].[K+].[K+].[CH3:56]N(C=O)C>[Cl-].[Na+].O.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>[Cl:39][C:40]1[CH:41]=[CH:42][C:43]([F:49])=[C:44]([C:28]2[CH:27]=[CH:26][C:25]([C:50]([O:51][CH3:56])=[O:53])=[CH:24][C:23]=2[C:20]2[C:19]([CH3:18])([CH3:32])[CH2:17][CH2:22][CH:21]=2)[CH:45]=1

참가 물질

7

반응물 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 3718925(5-Chloro-2-fluoro-phenyl)boronic acidHCID 57705953HCID 57705953, 화합물

생성물 1

HCID 57706006Methyl 5'-chloro-2-(5,5-dimethyl-1-cyclopenten-1-yl)-2'-fluoro-1,1'-biphenyl-4-carboxylate수율 86%

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 57417360Sodium chloride; water용매

반응 조건

온도
90 °C

실험 절차

To a stirred solution of methyl 3-(5,5-dimethylcyclopent-1-enyl)-4-(trifluoromethylsulfonyloxy)benzoate 66.61 (0.100 g, 0.3 mmol) in DMF (4 mL) at 23° C. was added 5-chloro-2-fluorophenylboronic acid (0.07 g, 0.4 mmol) (commercially available from Aldrich), potassium carbonate (0.1 g, 0.8 mmol), followed by tetrakis(triphenylphosphine)palladium (0.03 g, 0.03 mmol). The mixture was heated to 90° C. and stirring was continued for 23 hours. The reaction was then cooled to room temperature. The reaction was diluted with brine and extracted three times with EtOAc. After drying over anhydrous magnesium sulfate and filtering, the organic solvent was removed under reduced pressure and the product was purified on silica gel (0-10% EtOAc in hexanes) to yield 78.9A as a colorless oil (0.082 g, 86% yield).

후처리

  1. temperatureThe reaction was then cooled to room temperature
  2. extractionextracted three times with EtOAc
  3. dry with materialAfter drying over anhydrous magnesium sulfate
  4. filtrationfiltering
  5. customthe organic solvent was removed under reduced pressure
  6. customthe product was purified on silica gel (0-10% EtOAc in hexanes)

출처 및 근거

ORD 기록
ord-a7ebf87dedfc42cfbb1ef9bfaa7ba955
출처 데이터셋
uspto-grants-2011_10
특허 번호
US08030354B2

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