Dimethylformamide → 5-Bromopyridine-2-carbonitrile

HRID 2247228Notes

Reaction equation

HRID 2247228 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][N:3]=1.C(Cl)Cl.[CH3:12][N:13](C=O)C>O.[C-]#N.[Zn+2].[C-]#N.[Zn].C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[Br:8][C:5]1[CH:6]=[CH:7][C:2]([C:12]#[N:13])=[N:3][CH:4]=1

Participants

8

Reactant 3

HCID 6228DimethylformamideHCID 6344DichloromethaneHCID 693532,5-Dibromopyridine

Product 1

HCID 8171545-Bromopyridine-2-carbonitrile

Reagents, catalysts & solvents 4

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 23994ZincCatalystHCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 962WaterSolvent

Procedure

The mixture of 2,5-dibromopyridine (4.74 g, 20.0 mmol), zinc cyanide (1.40 g, 12.0 mmol), zinc dust (0.059 g, 0.90 mmol), and Pd(dppf)Cl2.CH2Cl2 (0.36 g, 0.44 mmol) in 25 ml of DMF was heated at reflux for 5 h, cooled to RT, diluted with H2O, extracted with EtOAc, the organic portion was washed with brine, the solvents were removed, the crude compound was purified by flash column chromatography (5 to 15% of EtOAc in hexanes), the titled compound was obtained as an off-white solid.

Workup

  1. temperatureat reflux for 5 h
  2. extractionextracted with EtOAc
  3. washthe organic portion was washed with brine
  4. customthe solvents were removed
  5. customthe crude compound was purified by flash column chromatography (5 to 15% of EtOAc in hexanes)

Sources & evidence

ORD record
ord-ba1bfdc02c3344c183beb6c0e005a269
Source dataset
uspto-grants-2010_03
Patent number
US07687643B2

Reaction notes

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