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

HRID 17344

반응식

HRID 17344 반응식
[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]

참가 물질

6

반응물 2

HCID 11430Potassium Carbonate2회HCID 510414276-Bromo-2-cyclopropyl-7-fluoro-5-methylbenzoxazole-4-carbonitrile

생성물 1

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

시약·촉매·용매 3

HCID 887Methanol용매2회HCID 962Water용매2회HCID 6228Dimethylformamide용매2회

반응 조건

온도
60 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-4d1810d08b1f4792920fd4ab68f8ca7d
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07737166B2

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