Water → 6,7-Dimethoxy-4-(7-phenyl-benzothiazol-6-yloxy)-quinoline

HRID 228861노트

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HRID 228861 반응식
I[C:2]1[C:10]2[S:9][CH:8]=[N:7][C:6]=2[CH:5]=[CH:4][C:3]=1[O:11][C:12]1[C:21]2[C:16](=[CH:17][C:18]([O:24][CH3:25])=[C:19]([O:22][CH3:23])[CH:20]=2)[N:15]=[CH:14][CH:13]=1.[C:26]1(B(O)O)[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[CH3:23][O:22][C:19]1[CH:20]=[C:21]2[C:16](=[CH:17][C:18]=1[O:24][CH3:25])[N:15]=[CH:14][CH:13]=[C:12]2[O:11][C:3]1[CH:4]=[CH:5][C:6]2[N:7]=[CH:8][S:9][C:10]=2[C:2]=1[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 66827Phenylboronic AcidHCID 230783324-(7-Iodo-benzothiazol-6-yloxy)-6,7-dimethoxy-quinoline2회

생성물 1

HCID 230782936,7-Dimethoxy-4-(7-phenyl-benzothiazol-6-yloxy)-quinoline수율 98%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
80 °C

실험 절차

4-(7-Iodo-benzothiazol-6-yloxy)-6,7-dimethoxy-quinoline (compound 294) (40 mg), phenylboronic acid (40 mg), and tetrakistriphenylphosphine palladium (20 mg) were dissolved in N,N-dimethylformamide (5 ml) to prepare a solution. A 2 M aqueous potassium carbonate solution (0.3 ml) was added to the reaction system, and the mixture was stirred at 80° C. for 20 min. Water was added to the reaction solution, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was then washed with water and was dried over anhydrous sodium sulfate. The solvent was removed by distillation under the reduced pressure, and the residue was purified by thin layer chromatography using acetone-chloroform to give the title compound (35 mg, yield 98%).

후처리

  1. customto prepare a solution
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe ethyl acetate layer was then washed with water
  4. dry with materialwas dried over anhydrous sodium sulfate
  5. customThe solvent was removed by distillation under the reduced pressure
  6. customthe residue was purified by thin layer chromatography

출처 및 근거

ORD 기록
ord-83bd29e4a25d41dba88e9878e03c2759
출처 데이터셋
uspto-grants-2009_07
특허 번호
US07560558B2

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