Dimethylformamide → HCID 67440151, compound

HRID 1255703Notes

Reaction equation

HRID 1255703 reaction equation
Cl[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([O:10][CH3:11])[N:3]=1.[Br:12][C:13]1[CH:18]=[CH:17][C:16]([OH:19])=[C:15]([F:20])[C:14]=1[CH:21]1[O:25][CH2:24][CH2:23][O:22]1.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[Br:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][C:2]2[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([O:10][CH3:11])[N:3]=2)=[C:15]([F:20])[C:14]=1[CH:21]1[O:22][CH2:23][CH2:24][O:25]1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 143811116-Chloro-2-methoxynicotinonitrileHCID 67440478HCID 67440478, compound

Product 1

HCID 67440151HCID 67440151, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 6-chloro-2-methoxynicotinonitrile (1.16 g, 6.88 mmol), 4-bromo-3-(1,3-dioxolan-2-yl)-2-fluorophenol (1.81 g, 6.88 mmol), potassium carbonate (1.14 g, 8.26 mmol), and N,N-dimethylformamide (35 mL) was stirred at 80° C. overnight. Water was added and the solution was extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate, and filtered. The solvent was removed under reduced pressure and the residue was purified by silica gel column using Combiflash to give 6-(4-bromo-3-(1,3-dioxolan-2-yl)-2-fluorophenoxy)-2-methoxynicotinonitrile (2.31 g, 85% yield).

Workup

  1. extractionthe solution was extracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. customThe solvent was removed under reduced pressure
  6. customthe residue was purified by silica gel column

Sources & evidence

ORD record
ord-136b8db6f25e4e689c4c31a613526ed1
Source dataset
uspto-grants-2013_06
Patent number
US08461135B2

Reaction notes

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