Sodium Carbonate → 2-Fluoro-3-{3-[(trimethylsilyl)ethynyl]phenyl}pyridine

HRID 646222

반응식

HRID 646222 반응식
Br[C:2]1[CH:3]=[C:4]([C:8]#[C:9][Si:10]([CH3:13])([CH3:12])[CH3:11])[CH:5]=[CH:6][CH:7]=1.[F:14][C:15]1[C:20](B(O)O)=[CH:19][CH:18]=[CH:17][N:16]=1.C(=O)([O-])[O-].[Na+].[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:14][C:15]1[C:20]([C:2]2[CH:7]=[CH:6][CH:5]=[C:4]([C:8]#[C:9][Si:10]([CH3:13])([CH3:12])[CH3:11])[CH:3]=2)=[CH:19][CH:18]=[CH:17][N:16]=1

참가 물질

7

반응물 3

HCID 10340Sodium CarbonateHCID 27832702-Fluoropyridine-3-boronic acidHCID 3683324((3-Bromophenyl)ethynyl)trimethylsilane

생성물 1

HCID 687015872-Fluoro-3-{3-[(trimethylsilyl)ethynyl]phenyl}pyridine수율 92.8%

시약·촉매·용매 3

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

실험 절차

To a solution of [(3-bromophenyl)ethynyl](trimethyl)silane (2.28 g, 9.0 mmol) in DME (150 mL) is added (2-fluoropyridin-3-yl)boronic acid (1.41 g, 10.0 mmol), tetrakis(triphenylphosphine)palladium (0.52 g, 0.5 mmol) and a solution of sodium carbonate (3.8 g, 36.0 mmol) in H2O (15 mL) at room temperature. After refluxing for 3 h, the reaction mixture is cooled, quenched with saturated sodium carbonate, diluted with EtOAc. The two layers are separated and the aqueous layer is extracted with EtOAc. The combined organic extracts are washed with brine, dried (MgSO4) and concentrated. The crude mixture is purified by chromatography (silica gel, EtOAc/hexane:5/95) to give the 2-fluoro-3-{3-[(trimethylsilyl)ethynyl]phenyl}pyridine (2.25 g, 91%) as an oil. MS (+) APPI: 270 (M+H)+.

후처리

  1. customat room temperature
  2. temperatureAfter refluxing for 3 h
  3. temperaturethe reaction mixture is cooled
  4. customquenched with saturated sodium carbonate
  5. additiondiluted with EtOAc
  6. customThe two layers are separated
  7. extractionthe aqueous layer is extracted with EtOAc
  8. washThe combined organic extracts are washed with brine
  9. dry with materialdried (MgSO4)
  10. concentrationconcentrated
  11. customThe crude mixture is purified by chromatography (silica gel, EtOAc/hexane:5/95)

출처 및 근거

ORD 기록
ord-4b3c217f41ab446ba3f4c2cdb1c4c294
출처 데이터셋
uspto-grants-2010_04
특허 번호
US07705030B2

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