Triethylborane → HCID 21928368, compound

HRID 1243621Notes

Reaction equation

HRID 1243621 reaction equation
[Cl:1][C:2]1[C:7]([C:8]#[N:9])=[CH:6][C:5]([F:10])=[C:4](Cl)[N:3]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].[CH2:20](B(CC)CC)[CH3:21]>C1COCC1.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]>[Cl:1][C:2]1[C:7]([C:8]#[N:9])=[CH:6][C:5]([F:10])=[C:4]([CH2:20][CH3:21])[N:3]=1

Participants

6

Reactant 3

HCID 7357TriethylboraneHCID 62657Potassium Phosphate, TribasicHCID 27338492,6-Dichloro-5-fluoro-3-pyridinecarbonitrile

Product 1

HCID 21928368HCID 21928368, compound

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

To a vigorously stirred mixture of 2,6-dichloro-5-fluoro-3-pyridinecarbonitrile (15.0 g, 78.5 mmol), potassium phosphate (17.0 g, 74.0 mmol), and [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (1.5 g, 1.8 mmol) in dry THF (300 ml) at room temperature was added in a stream triethylborane (85 ml of a 1M solution in THF). The resulting mixture was heated at reflux temperature for 16 h, cooled, concentrated, and partitioned between ethyl acetate and water. The resulting crude product obtained from the organics was subjected to flash chromatography using ethyl acetate/hexanes as eluent to give the title compound (8 g) as a solid.

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureat reflux temperature for 16 h
  3. temperaturecooled
  4. concentrationconcentrated
  5. custompartitioned between ethyl acetate and water
  6. customThe resulting crude product obtained from the

Sources & evidence

ORD record
ord-ab2f9b1f57e6444f915bce04d8ece7d8
Source dataset
uspto-grants-2006_10
Patent number
US07119109B2

Reaction notes

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