Sodium Cyanide → HCID 67047732, compound

HRID 606913Notes

Reaction equation

HRID 606913 reaction equation
Cl[CH2:2][C:3]1[CH:4]=[C:5]([C:10]#[C:11][C:12]2[CH:13]=[N:14][CH:15]=[C:16]([CH:19]=2)[C:17]#[N:18])[CH:6]=[CH:7][C:8]=1[F:9].[C-:20]#[N:21].[Na+]>CN(C)C=O.C(OCC)(=O)C>[C:20]([CH2:2][C:3]1[CH:4]=[C:5]([C:10]#[C:11][C:12]2[CH:13]=[N:14][CH:15]=[C:16]([CH:19]=2)[C:17]#[N:18])[CH:6]=[CH:7][C:8]=1[F:9])#[N:21]

Participants

5

Reactant 2

HCID 8929Sodium CyanideHCID 67047920HCID 67047920, compound

Product 1

HCID 67047732HCID 67047732, compoundYield 78.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Dissolve 5-(3-chloromethyl-4-fluorophenylethynyl)-nicotinonitrile, (prepared as described in PREPARATION 32), (120 mg, 0.44 mmol) in N,N-dimethylformamide (2.2 mL) and treat with sodium cyanide (86 mg, 1.8 mmol). After stirring for 30 min at room temperature, dilute with ethyl acetate and wash with an aqueous saturated solution of sodium bicarbonate and an aqueous saturated solution of sodium chloride. Dry (sodium sulfate), filter, and concentrate. Purify by silica gel chromatography, eluting with 70:30 hexanes:ethyl acetate, to give the title compound as a white crystalline solid (90 mg, 78%).

Workup

  1. washwash with an aqueous saturated solution of sodium bicarbonate
  2. dry with materialDry (sodium sulfate)
  3. filtrationfilter
  4. concentrationconcentrate
  5. customPurify by silica gel chromatography
  6. washeluting with 70:30 hexanes

Sources & evidence

ORD record
ord-08d234cf7da14cf0acd4ed2b9801330d
Source dataset
uspto-grants-2011_03
Patent number
US07915424B2

Reaction notes

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