Potassium Phosphate, Tribasic → HCID 58042362、化合物

HRID 512074ノート

反応式

HRID 512074 の反応式
[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

参加物

6

反応物 4

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

生成物 1

HCID 58042362HCID 58042362、化合物収率 59%

試薬・触媒・溶媒 1

HCID 167845palladium(II) acetate触媒

反応条件

温度
80 °C

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-d14d6e96ce4e482899074c5a1803dd8e
出典データセット
uspto-grants-2015_08
特許番号
US09102621B2

反応ノート

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