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

HRID 243875

반응식

HRID 243875 반응식
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]

참가 물질

7

반응물 3

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

생성물 1

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

시약·촉매·용매 3

HCID 178418397HCID 178418397, 화합물촉매HCID 962Water용매HCID 80711,2-Dimethoxyethane용매

반응 조건

온도
23 °C

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-a08601227d3d4cc4a757065d38125524
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08653263B2

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