4-Cyanopyridine → HCID 58830624, compound

HRID 2353384Notes

Reaction equation

HRID 2353384 reaction equation
Br[C:2]1[CH:7]=[C:6]([F:8])[C:5]([Br:9])=[CH:4][C:3]=1[F:10].C([Li])CCC.[C:16]([C:18]1[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=1)#[N:17].[Cl-].[NH4+]>C(OCC)C>[Br:9][C:5]1[C:6]([F:8])=[CH:7][C:2]([C:16]([C:18]2[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=2)=[NH:17])=[C:3]([F:10])[CH:4]=1

Participants

6

Reactant 4

HCID 75064-CyanopyridineHCID 25517Ammonium ChlorideHCID 675961,4-Dibromo-2,5-difluorobenzeneHCID 178418339Butyllithium

Product 1

HCID 58830624HCID 58830624, compoundYield 50.5%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A stirred solution of 1,4-dibromo-2,5-difluorobenzene (2.72 g) in anhydrous diethylether (50 ml) under nitrogen was cooled to −78° C. in a dry-ice/acetone bath then treated with n-butyllithium (1.6M in hexanes, 7.2 ml). The reaction mixture was stirred for 20 min and a solution of 4-cyanopyridine (1.4 g) in diethylether (60 ml) was added dropwise. The resulting mixture was stirred for a further 20 min then treated with saturated aqueous ammonium chloride. The ether layer was separated, washed with brine, dried (sodium sulfate) and concentrated under vacuum. The crude product was purified on an SPE cartridge (silica) using a cyclohexane/ethyl acetate gradient as eluant to give the title compound as a colourless gum (1.50 g).

Workup

  1. stirringThe resulting mixture was stirred for a further 20 min
  2. customThe ether layer was separated
  3. washwashed with brine
  4. dry with materialdried (sodium sulfate)
  5. concentrationconcentrated under vacuum
  6. customThe crude product was purified on an SPE cartridge (silica)

Sources & evidence

ORD record
ord-35ab20f725944133bc2da103eec90526
Source dataset
uspto-grants-2010_07
Patent number
US07750026B2

Reaction notes

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