Potassium Carbonate → 6-Bromo-2-cyclopropyl-7-methoxy-5-methyl-1,3-benzoxazole-4-carbonitrile

HRID 17344

Reaction equation

HRID 17344 reaction equation
[Br:1][C:2]1[C:3](F)=[C:4]2[O:8][C:7]([CH:9]3[CH2:11][CH2:10]3)=[N:6][C:5]2=[C:12]([C:15]#[N:16])[C:13]=1[CH3:14].[C:18](=O)([O-])[O-:19].[K+].[K+]>O.CN(C)C=O.CO>[Br:1][C:2]1[C:3]([O:19][CH3:18])=[C:4]2[O:8][C:7]([CH:9]3[CH2:11][CH2:10]3)=[N:6][C:5]2=[C:12]([C:15]#[N:16])[C:13]=1[CH3:14]

Participants

6

Reactant 2

HCID 11430Potassium Carbonate2×HCID 510414276-Bromo-2-cyclopropyl-7-fluoro-5-methylbenzoxazole-4-carbonitrile

Product 1

HCID 685847456-Bromo-2-cyclopropyl-7-methoxy-5-methyl-1,3-benzoxazole-4-carbonitrileYield 64%

Reagents, catalysts & solvents 3

HCID 887MethanolSolvent2×HCID 962WaterSolvent2×HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
60 °C

Procedure

6-Bromo-2-cyclopropyl-7-fluoro-5-methyl-1,3-benzoxazole-4-carbonitrile (I-77) (4.88 g, 16.5 mmol) was suspended in a mixed solvent of methanol (30 ml) and N,N-dimethylformamide (50 ml), potassium carbonate (4.57 g, 33.0 mmol) was added, followed by stirring at 60° C. for 30 minutes. With cooling with ice, water was added, followed by extraction with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, the solvent was evaporated away. The residue was suspended in a mixed solvent of methanol (30 ml) and N,N-dimethylformamide (50 ml), potassium carbonate (4.57 g, 33.0 mmol) was added, followed by again stirring at 60° C. for 14 hours. With cooling with ice, water was added, followed by extraction with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, the solvent was evaporated away. The precipitated solid was washed with a mixed solvent of ethyl acetate/isopropyl ether and collected by filtration to obtain the entitled compound (2.599 g, 64%) as a colorless solid.

Workup

  1. additionwas added
  2. additionwas added
  3. extractionfollowed by extraction with ethyl acetate
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customthe solvent was evaporated away
  7. additionwas added
  8. stirringby again stirring at 60° C. for 14 hours
  9. additionwas added
  10. extractionfollowed by extraction with ethyl acetate
  11. washThe organic layer was washed with saturated brine
  12. dry with materialdried over anhydrous sodium sulfate
  13. customthe solvent was evaporated away
  14. washThe precipitated solid was washed with a mixed solvent of ethyl acetate/isopropyl ether
  15. filtrationcollected by filtration

Sources & evidence

ORD record
ord-4d1810d08b1f4792920fd4ab68f8ca7d
Source dataset
uspto-grants-2010_06
Patent number
US07737166B2

Linked notes

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