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

HRID 646222

Reaction equation

HRID 646222 reaction equation
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

Participants

7

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

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)+.

Workup

  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)

Sources & evidence

ORD record
ord-4b3c217f41ab446ba3f4c2cdb1c4c294
Source dataset
uspto-grants-2010_04
Patent number
US07705030B2

Linked notes

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