Dimethylformamide → 5-Bromo-2-ethoxy-6-(4-fluorophenyl)nicotinonitrile

HRID 531032Notes

Reaction equation

HRID 531032 reaction equation
I[CH2:2][CH3:3].[Br:4][C:5]1[C:6]([C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=2)=[N:7][C:8]([OH:13])=[C:9]([CH:12]=1)[C:10]#[N:11].C(=O)([O-])[O-].[K+].[K+].CN(C=O)C>O>[Br:4][C:5]1[C:6]([C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=2)=[N:7][C:8]([O:13][CH2:2][CH3:3])=[C:9]([CH:12]=1)[C:10]#[N:11]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 178509436HCID 178509436, compound

Product 1

HCID 1179921125-Bromo-2-ethoxy-6-(4-fluorophenyl)nicotinonitrile

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Iodoethane (1.43 mL) was added to a mixture of 5-bromo-6-(4-fluorophenyl)-2-hydroxynicotinonitrile (3.49 g), potassium carbonate (3.29 g), and DMF (30 mL), and the resultant mixture was stirred at 80° C. for 30 minutes. Water was added to the reaction mixture, followed by extraction with ethyl acetate. The organic layer was washed with saturated saline and dried over anhydrous magnesium sulfate, and then, the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate) to obtain the title compound (3.00 g).

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe organic layer was washed with saturated saline
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-3102067dd94d477d96c3a759f3914152
Source dataset
uspto-grants-2016_05
Patent number
US09353108B2

Reaction notes

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