Potassium Phosphate, Tribasic → HCID 58042362, 화합물

HRID 512074노트

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HRID 512074 반응식
[CH:1]1(B(O)O)[CH2:3][CH2:2]1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].Br[C:16]1[C:21]([O:22][CH:23]([F:25])[F:24])=[CH:20][CH:19]=[CH:18][N:17]=1.C1(P(C2CCCCC2)C2CCCCC2)CCCCC1>C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH:1]1([C:16]2[C:21]([O:22][CH:23]([F:25])[F:24])=[CH:20][CH:19]=[CH:18][N:17]=2)[CH2:3][CH2:2]1

참가 물질

6

반응물 4

HCID 62657Potassium Phosphate, TribasicHCID 75806TricyclohexylphosphineHCID 2760897Cyclopropylboronic acidHCID 580424482-broMo-3-(difluoroMethoxy)pyridine

생성물 1

HCID 58042362HCID 58042362, 화합물수율 59%

시약·촉매·용매 1

HCID 167845palladium(II) acetate촉매

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온도
80 °C

실험 절차

Cyclopropylboronic acid (383 mg, 4.5 mmol) and potassium phosphate tribasic (1.89 g, 8.9 mmol) were added to a solution of 2-bromo-3-difluoromethoxypyridine (Preparation 102, 570 mg, 2.5 mmol). The mixture was heated to 80° C. and degassed thoroughly by bubbling nitrogen through the mixture. After 30 minutes, the reaction was heated to 95° C. and tricyclohexylphosphine (84 mg, 0.30 mmol) was added followed by palladium acetate (32 mg, 0.14 mmol). The reaction was stirred at 95° C. for 18 hours then cooled to room temperature. The mixture was filtered through arbocel, washing with EtOAc and the filtrate concentrated in vacuo. The residue was then purified by flash column chromatography eluting with EtOAc:heptane 1:5 to afford the title compound as a colourless oil (273 mg, 58%).

후처리

  1. customdegassed thoroughly
  2. customby bubbling nitrogen through the mixture
  3. temperaturethe reaction was heated to 95° C.
  4. temperaturethen cooled to room temperature
  5. filtrationThe mixture was filtered through arbocel
  6. washwashing with EtOAc
  7. concentrationthe filtrate concentrated in vacuo
  8. customThe residue was then purified by flash column chromatography
  9. washeluting with EtOAc:heptane 1:5

출처 및 근거

ORD 기록
ord-d14d6e96ce4e482899074c5a1803dd8e
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09102621B2

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