Methyl iodide → 5-Methoxy-7-methyl-3-(3-trifluoromethylphenyl)cinnoline

HRID 229732노트

반응식

HRID 229732 반응식
[CH3:1][C:2]1[CH:3]=[C:4]([OH:22])[C:5]2[CH:6]=[C:7]([C:12]3[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:21])([F:20])[F:19])[CH:13]=3)[N:8]=[N:9][C:10]=2[CH:11]=1.CI.[C:25](=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH3:25][O:22][C:4]1[CH:3]=[C:2]([CH3:1])[CH:11]=[C:10]2[C:5]=1[CH:6]=[C:7]([C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:21])([F:20])[F:19])[CH:13]=1)[N:8]=[N:9]2

참가 물질

5

반응물 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 1354580247-Methyl-3-(3-trifluoromethylphenyl)cinnolin-5-ol

생성물 1

HCID 230867125-Methoxy-7-methyl-3-(3-trifluoromethylphenyl)cinnoline수율 15.7%

시약·촉매·용매 1

HCID 180Acetone용매

실험 절차

To an acetone solution (5 mL) of 7-methyl-3-(3-trifluoromethylphenyl)cinnolin-5-ol (30.4 mg, 0.1 mmol) obtained in Example 70 were added methyl iodide (0.006 mL, 0.11 mmol) and potassium carbonate (13.8 mg, 0.11 mmol), followed by reaction at room temperature over night. To residue obtained by concentration of the reaction liquid under reduced pressure was added distilled water (1 mL) and extracted with ethyl acetate. Residue obtained after concentration of an organic layer under reduced pressure was purified with silica gel column chromatography (hexane/ethyl acetate=1/1) to obtain an objective compound (5 mg, 15%) as white solid.

후처리

  1. customfollowed by reaction at room temperature over night
  2. customTo residue obtained by concentration of the reaction liquid under reduced pressure
  3. additionwas added
  4. distillationdistilled water (1 mL)
  5. extractionextracted with ethyl acetate
  6. customResidue obtained after concentration of an organic layer under reduced pressure
  7. customwas purified with silica gel column chromatography (hexane/ethyl acetate=1/1)

출처 및 근거

ORD 기록
ord-71d04ee12efc4282aab2c31c6b5e221b
출처 데이터셋
uspto-grants-2009_07
특허 번호
US07563893B2

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