2,5-Dibromopyridine → 5-Bromo-3'-fluoro-2,4'-bipyridine

HRID 42022

Reaction equation

HRID 42022 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][N:3]=1.[F:9][C:10]1[CH:11]=[N:12][CH:13]=[CH:14][C:15]=1[Sn](CCCC)(CCCC)CCCC>CN(C=O)C.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.[Cu]I>[Br:8][C:5]1[CH:6]=[CH:7][C:2]([C:15]2[CH:14]=[CH:13][N:12]=[CH:11][C:10]=2[F:9])=[N:3][CH:4]=1

Participants

6

Reactant 2

HCID 693532,5-DibromopyridineHCID 222736013-Fluoro-4-(tributylstannyl)pyridine

Product 1

HCID 584158125-Bromo-3'-fluoro-2,4'-bipyridineYield 62%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
130 °C

Procedure

In a schlenck tube, a mixture of 2,5-dibromopyridine (2.11 mmol, 0.500 g), 3-fluoro-4-(tributylstannyl)pyridine (2.32 mmol, 0.896 g), PdCl2(PPh3)2 (0.21 mmol, 0.148 g), CuI (0.43 mmol, 0.080 g) in DMF (5 ml) was heated at 130° C. for 12 hours, under argon atmosphere. The solvent was evaporated and the crude mixture was extracted between water and ethyl acetate. The solid residue was purified by chromatography over SiO2 eluting with DCM/methanol mixtures affording 0.330 g (yield 62%) of the expected product.

Workup

  1. customThe solvent was evaporated
  2. extractionthe crude mixture was extracted between water and ethyl acetate
  3. customThe solid residue was purified by chromatography over SiO2 eluting with DCM/methanol

Sources & evidence

ORD record
ord-a11cea2e8f2340d298289a02033d0720
Source dataset
uspto-grants-2013_09
Patent number
US08536165B2

Linked notes

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