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

HRID 243877

반응식

HRID 243877 반응식
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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
23 °C

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-98d9399d610b413bab494ad585f968fc
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08653263B2

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