Dimethylformamide → HCID 67440151, compound

HRID 1471560Notes

Reaction equation

HRID 1471560 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 674404784-Bromo-3-(1,3-dioxolan-2-yl)-2-fluorophenol

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-a2a5adf6181b47f1822ac04c2dbce3c6
Source dataset
uspto-grants-2015_04
Patent number
US09012431B2

Reaction notes

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