1,2-Dimethoxyethane → methyl 5-fluoro-2-(1H-pyrazol-5-yl)benzoate

HRID 243877

反応式

HRID 243877 の反応式
C[C:2]1[CH:10]=[CH:9][C:5](C([O-])=O)=[C:4]([F:11])[C:3]=1Br.[NH:13]1[C:17](B(O)O)=[CH:16][CH:15]=[N:14]1.[C:21]([O-:24])(O)=[O:22].[Na+].[CH3:26]OCCOC>O>[F:11][C:4]1[CH:3]=[CH:2][C:10]([C:17]2[NH:13][N:14]=[CH:15][CH:16]=2)=[C:9]([CH:5]=1)[C:21]([O:24][CH3:26])=[O:22]

参加物

6

反応物 4

HCID 80711,2-DimethoxyethaneHCID 516892Sodium BicarbonateHCID 112519791H-Pyrazole-5-boronic acidHCID 53430578Methyl-2-fluoro-bromobenzoate

生成物 1

HCID 67086678methyl 5-fluoro-2-(1H-pyrazol-5-yl)benzoate収率 44%

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
23 °C

実験手順

Methyl-2-fluoro-bromobenzoate (1.0 gram, 4.2 mmol) and (1H-pyrazol-5-yl)boronic acid (485 mg, 4.6 mmol) were combined and dissolved in degassed DME (15 mL) then treated with NaHCO3 (706 mg, 8.4 mmol) in water and the reaction purged with bubbling N2 for 5 minutes. The reaction was treated with Pd(PPh3)4 (243 mg (0.2 mmol) and then purged with bubbling for 5 minutes in a sealed vessel and then heated to reflux for 2 h. The reaction mixture was cooled to 23° C., filtered, and the solid was rinsed with EtOAc and the layers separated. The organic layers were combined, dried and concentrated. Chromatography (ethyl acatate/hexanes, 0-30%) gave methyl 5-fluoro-2-(1H-pyrazol-5-yl)benzoate (415 mg, 44%).

後処理

  1. customthe reaction purged with bubbling N2 for 5 minutes
  2. additionThe reaction was treated with Pd(PPh3)4 (243 mg (0.2 mmol)
  3. custompurged
  4. customwith bubbling for 5 minutes in a sealed vessel
  5. temperatureheated
  6. temperatureto reflux for 2 h
  7. filtrationfiltered
  8. washthe solid was rinsed with EtOAc
  9. customthe layers separated
  10. customdried
  11. concentrationconcentrated

出典と根拠

ORDレコード
ord-98d9399d610b413bab494ad585f968fc
出典データセット
uspto-grants-2014_02
特許番号
US08653263B2

関連ノート

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