Sodium Carbonate → 2-Fluoro-2'-(trifluoromethyl)-3,4'-bipyridine

HRID 473624Notes

Reaction equation

HRID 473624 reaction equation
[F:1][C:2]1[C:7](B(O)O)=[CH:6][CH:5]=[CH:4][N:3]=1.Br[C:12]1[CH:17]=[CH:16][N:15]=[C:14]([C:18]([F:21])([F:20])[F:19])[CH:13]=1.C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.C(O)C.O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[F:1][C:2]1[C:7]([C:12]2[CH:17]=[CH:16][N:15]=[C:14]([C:18]([F:21])([F:20])[F:19])[CH:13]=2)=[CH:6][CH:5]=[CH:4][N:3]=1

Participants

8

Reactant 3

HCID 10340Sodium CarbonateHCID 27832702-Fluoropyridine-3-boronic acidHCID 234369504-Bromo-2-(trifluoromethyl)pyridine

Product 1

HCID 593269242-Fluoro-2'-(trifluoromethyl)-3,4'-bipyridine

Reagents, catalysts & solvents 4

HCID 178418476HCID 178418476, compoundCatalystHCID 702EthanolSolventHCID 962WaterSolvent2×HCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
95 °C

Procedure

A mixture of 2-fluoropyridin-3-ylboronic acid (0.748 g, 5.3 mmol), 4-bromo-2-(trifluoromethyl)pyridine (1.00 g, 4.4 mmol), Pd(PPh3)2Cl2 (0.155 g, 0.22 mmol) and sodium carbonate (0.797 g, 13.3 mmol) in DME (6.5 mL), ethanol (1.9 mL) and water (0.47 mL) was heated to 95° C. for 2 h. After cooling to room temperature, the mixture was diluted with H2O and extracted with CH2Cl2 (3×). The combined organics were dried over Na2SO4, filtered and concentrated. The residue was purified using column chromatography (EtOAc/Hexanes=0→20%) to give the title compound. MS (ESI, pos. ion) m/z: 243 (M+1).

Workup

  1. temperatureAfter cooling to room temperature
  2. extractionextracted with CH2Cl2 (3×)
  3. dry with materialThe combined organics were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified

Sources & evidence

ORD record
ord-982a471bee604723b4b7c88e00e160e7
Source dataset
uspto-grants-2014_01
Patent number
US08637500B2

Reaction notes

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