Potassium Cyanide → HCID 18385060, compound

HRID 2298247Notes

Reaction equation

HRID 2298247 reaction equation
Br[CH2:2][CH2:3][CH2:4][N:5]1[C:13]2[C:8](=[CH:9][C:10]([F:14])=[CH:11][CH:12]=2)[C:7]([N:15]2[C:19]([C:20]3[C:28]4[C:23](=[CH:24][CH:25]=[C:26]([F:29])[CH:27]=4)[N:22]([CH3:30])[CH:21]=3)=[N:18][NH:17][C:16]2=[O:31])=[CH:6]1.[C-:32]#[N:33].[K+]>CN(C=O)C>[F:14][C:10]1[CH:9]=[C:8]2[C:13](=[CH:12][CH:11]=1)[N:5]([CH2:4][CH2:3][CH2:2][C:32]#[N:33])[CH:6]=[C:7]2[N:15]1[C:16](=[O:31])[NH:17][N:18]=[C:19]1[C:20]1[C:28]2[C:23](=[CH:24][CH:25]=[C:26]([F:29])[CH:27]=2)[N:22]([CH3:30])[CH:21]=1

Participants

4

Reactant 2

HCID 9032Potassium CyanideHCID 18385099HCID 18385099, compound

Product 1

HCID 18385060HCID 18385060, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of the product from Example 18 (0.86 g, 1.77 mmol) in dry DMF (25 mL) was added potassium cyanide (0.18 g, 2.77 mmol) and the mixture was stirred and heated at 50° C. overnight under nitrogen. The solvent was evaporated, and the residue was distributed between ethyl acetate and water. The water phase was extracted twice with ethyl acetate, and the combined organic phases were washed with water and dried. After evaporation the crude product was chromatographed on silica gel (EtOAc) to yield 0.46 g (61%) of the title product.

Workup

  1. customThe solvent was evaporated
  2. extractionThe water phase was extracted twice with ethyl acetate
  3. washthe combined organic phases were washed with water
  4. customdried
  5. customAfter evaporation the crude product
  6. customwas chromatographed on silica gel (EtOAc)

Sources & evidence

ORD record
ord-31242afce7fd49fea84ffc87232c0985
Source dataset
uspto-grants-2002_12
Patent number
US06492406B1

Reaction notes

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