Dimethylformamide → 5-Bromo-6-(4-fluorophenyl)-2-isopropoxynicotinonitrile

HRID 530994Notes

Reaction equation

HRID 530994 reaction equation
Br[CH:2]([CH3:4])[CH3:3].[Br:5][C:6]1[C:7]([C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=2)=[N:8][C:9]([OH:14])=[C:10]([CH:13]=1)[C:11]#[N:12].C(=O)([O-])[O-].[K+].[K+].CN(C=O)C>O>[Br:5][C:6]1[C:7]([C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=2)=[N:8][C:9]([O:14][CH:2]([CH3:4])[CH3:3])=[C:10]([CH:13]=1)[C:11]#[N:12]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 63582-BromopropaneHCID 11430Potassium CarbonateHCID 178509436HCID 178509436, compound

Product 1

HCID 1179921785-Bromo-6-(4-fluorophenyl)-2-isopropoxynicotinonitrile

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2-Bromopropane (3.32 mL) was added to a mixture of 5-bromo-6-(4-fluorophenyl)-2-hydroxynicotinonitrile (5.18 g), potassium carbonate (4.89 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 (5.92 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-058a6206ab544fb8a205605cac0e9a80
Source dataset
uspto-grants-2016_05
Patent number
US09353108B2

Reaction notes

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