Water → HCID 67501770, compound

HRID 1625208Notes

Reaction equation

HRID 1625208 reaction equation
[H-].[Na+].[F:3][C:4]([F:25])([F:24])[C:5]1[C:13]2[C:8](=[N:9][CH:10]=[CH:11][C:12]=2[C:14]2[CH:15]=[N:16][C:17]3[C:22]([CH:23]=2)=[CH:21][CH:20]=[CH:19][CH:18]=3)[NH:7][N:6]=1.[Br:26][C:27]1[CH:34]=[C:33](F)[CH:32]=[CH:31][C:28]=1[C:29]#[N:30].O>CN(C)C=O>[Br:26][C:27]1[CH:34]=[C:33]([N:7]2[C:8]3=[N:9][CH:10]=[CH:11][C:12]([C:14]4[CH:15]=[N:16][C:17]5[C:22]([CH:23]=4)=[CH:21][CH:20]=[CH:19][CH:18]=5)=[C:13]3[C:5]([C:4]([F:24])([F:3])[F:25])=[N:6]2)[CH:32]=[CH:31][C:28]=1[C:29]#[N:30]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 1189392-Bromo-4-fluorobenzonitrileHCID 178506293HCID 178506293, compound

Product 1

HCID 67501770HCID 67501770, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Sodium hydride (0.183 g, a 55% dispersion in paraffin liquid) was added to a solution of compound (1d) (0.940 g) in N,N-dimethylformamide (hereinafter referred to as DMF, 6 mL) at room temperature, followed by stirring for 30 min. Subsequently, 2-bromo-4-fluorobenzonitrile (0.838 g) was added to the reaction solution, followed by stirring at 60° C. for 1 hr. After cooling, water was added to the reaction solution, followed by extraction with ethyl acetate. The organic layer was washed with water and saturated saline in this order and was dried over anhydrous sodium sulfate. After distillation of the solvent, the residue was purified by neutral silica gel column chromatography (chloroform/methanol) to obtain compound (1e) (0.56 g, 38%) as a white solid.

Workup

  1. customat room temperature
  2. stirringby stirring at 60° C. for 1 hr
  3. temperatureAfter cooling
  4. extractionfollowed by extraction with ethyl acetate
  5. washThe organic layer was washed with water and saturated saline in this order
  6. dry with materialwas dried over anhydrous sodium sulfate
  7. distillationAfter distillation of the solvent
  8. customthe residue was purified by neutral silica gel column chromatography (chloroform/methanol)

Sources & evidence

ORD record
ord-7d862ba486fe43bb8c0dda058497daf8
Source dataset
uspto-grants-2014_07
Patent number
US08779142B2

Reaction notes

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