Potassium Carbonate → 4-Ethenyl-3,8-difluoro-6-methoxyquinoline

HRID 638995노트

반응식

HRID 638995 반응식
Br[C:2]1[C:11]2[C:6](=[C:7]([F:14])[CH:8]=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][C:3]=1[F:15].C(=O)([O-])[O-].[K+].[K+].[CH:22](B)=[CH2:23]>COCCOC.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>[CH:22]([C:2]1[C:11]2[C:6](=[C:7]([F:14])[CH:8]=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][C:3]=1[F:15])=[CH2:23]

참가 물질

7

반응물 3

HCID 11430Potassium CarbonateHCID 685768324-Bromo-3,8-difluoro-6-methoxyquinolineHCID 178419161HCID 178419161, 화합물

생성물 1

HCID 590260924-Ethenyl-3,8-difluoro-6-methoxyquinoline수율 90%

시약·촉매·용매 3

HCID 178418397HCID 178418397, 화합물촉매HCID 962Water용매2회HCID 80711,2-Dimethoxyethane용매

실험 절차

4-Bromo-3,8-difluoro-6-(methoxy)quinoline (0.63 g, 2.3 mmol) in DME (26 mL) under argon, was treated with tetrakis(triphenylphosphine)palladium(0) (0.13 g, 0.115 mmol) and the mixture stirred at room temperature for 20 minutes. Anhydrous potassium carbonate (0.32 g, 2.3 mmol), water (7 mL), and vinylborane:pyridine complex (see F. Kerins and D O'Shea J. Org. Chem. 2002, 67, 4968-4971) (0.22 g, 0.92 mmol) were added and the mixture was heated at 100° C. for 2 hr. It was cooled, diluted with water and extracted with ether, dried over magnesium sulfate and evaporated to dryness. After work-up the product was chromatographed on silica gel, eluting with 10% methanol in DCM to afford a white solid (0.46 g, 90%). MS (+ve ion electrospray) m/z 221 (MH+).

후처리

  1. temperaturethe mixture was heated at 100° C. for 2 hr
  2. temperatureIt was cooled
  3. extractionextracted with ether
  4. dry with materialdried over magnesium sulfate
  5. customevaporated to dryness
  6. customAfter work-up the product was chromatographed on silica gel
  7. washeluting with 10% methanol in DCM

출처 및 근거

ORD 기록
ord-6d85d8f564a74eefa82a3f5dc902e62a
출처 데이터셋
uspto-grants-2010_04
특허 번호
US07691850B2

반응 노트

불러오는 중…