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

HRID 638995ノート

反応式

HRID 638995 の反応式
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]

参加物

7

反応物 3

HCID 11430Potassium CarbonateHCID 685768324-Bromo-3,8-difluoro-6-methoxyquinolineHCID 178419161HCID 178419161、化合物

生成物 1

HCID 590260924-Ethenyl-3,8-difluoro-6-methoxyquinoline収率 90%

試薬・触媒・溶媒 3

HCID 178418397HCID 178418397、化合物触媒HCID 962Water溶媒2 回HCID 80711,2-Dimethoxyethane溶媒

実験手順

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+).

後処理

  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

出典と根拠

ORDレコード
ord-6d85d8f564a74eefa82a3f5dc902e62a
出典データセット
uspto-grants-2010_04
特許番号
US07691850B2

反応ノート

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