Sodium Bicarbonate → 3-fluoro-2-(1H-pyrazol-5-yl)benzonitrile

HRID 243875

反応式

HRID 243875 の反応式
Br[C:2]1[C:9]([F:10])=[CH:8][CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[NH:11]1[C:15](B(O)O)=[CH:14][CH:13]=[N:12]1.C([O-])(O)=O.[Na+]>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>[F:10][C:9]1[C:2]([C:13]2[NH:12][N:11]=[CH:15][CH:14]=2)=[C:3]([CH:6]=[CH:7][CH:8]=1)[C:4]#[N:5]

参加物

7

反応物 3

HCID 516892Sodium BicarbonateHCID 27833932-Bromo-3-fluorobenzonitrileHCID 112519791H-Pyrazole-5-boronic acid

生成物 1

HCID 671169283-fluoro-2-(1H-pyrazol-5-yl)benzonitrile収率 20.7%

試薬・触媒・溶媒 3

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

反応条件

温度
23 °C

実験手順

2-Bromo-3-fluorobenzonitrile (1.0 g, 5.0 mmol) and (1H-pyrazol-5-yl)boronic acid (647 mg, 4.6 mmol) were combined and dissolved in degassed DME (15 mL) then treated with NaHCO3 (1260 mg, 8.4 mmol) in water and the reaction purged with bubbling N2 for 5 minutes. The reaction was treated with Pd(PPh3)4 (288 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 was then cooled to 23° C. filtered and the solids were rinsed with EtOAc and the layers separated. The organic layers were combined, dried and concentrated under reduced pressure. Chromatography (0-30% ethyl acatate/hexanes) afforded 3-fluoro-2-(1H-pyrazol-5-yl)benzonitrile (178 mg, 19%).

後処理

  1. customthe reaction purged with bubbling N2 for 5 minutes
  2. custompurged
  3. customwith bubbling for 5 minutes in a sealed vessel
  4. temperatureheated
  5. temperatureto reflux for 2 h
  6. filtrationfiltered
  7. washthe solids were rinsed with EtOAc
  8. customthe layers separated
  9. customdried
  10. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-a08601227d3d4cc4a757065d38125524
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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