Benzoic acid, 2-bromo-5-fluoro-, methyl ester → methyl 5-fluoro-2-(1H-pyrazol-5-yl)benzoate

HRID 243849

反応式

HRID 243849 の反応式
Br[C:2]1[CH:11]=[CH:10][C:9]([F:12])=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[NH:13]1[C:17](B(O)O)=[CH:16][CH:15]=[N:14]1.C([O-])(O)=O.[Na+]>COCCOC.O>[F:12][C:9]1[CH:10]=[CH:11][C:2]([C:15]2[NH:14][N:13]=[CH:17][CH:16]=2)=[C:3]([CH:8]=1)[C:4]([O:6][CH3:7])=[O:5]

参加物

6

反応物 3

HCID 138875Benzoic acid, 2-bromo-5-fluoro-, methyl esterHCID 516892Sodium BicarbonateHCID 112519791H-Pyrazole-5-boronic acid

生成物 1

HCID 67086678methyl 5-fluoro-2-(1H-pyrazol-5-yl)benzoate収率 44.9%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 80711,2-Dimethoxyethane溶媒

反応条件

温度
23 °C

実験手順

Methyl 2-bromo-5-fluorobenzoate (1.0 g, 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 solid rinsed with EtOAc. The organic layers were separated, dried and concentrated. Purification via FCC (ethyl acatate/hexanes, 0-30%) afforded 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. washsolid rinsed with EtOAc
  9. customThe organic layers were separated
  10. customdried
  11. concentrationconcentrated
  12. customPurification via FCC (ethyl acatate/hexanes, 0-30%)

出典と根拠

ORDレコード
ord-bb7166fd3d904c0d84d22df8de72cb8c
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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