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

HRID 2220444

反応式

HRID 2220444 の反応式
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

参加物

7

反応物 3

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

生成物 1

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

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

実験手順

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)+.

後処理

  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)

出典と根拠

ORDレコード
ord-a21f3320252e4dfdb49b4eeb051f8169
出典データセット
uspto-grants-2008_08
特許番号
US07417047B2

関連ノート

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