Cesium carbonate → 6-Benzyloxy-4-(4-fluoro-2-methylindol-5-yloxy)-7-methoxyquinazoline

HRID 916369노트

반응식

HRID 916369 반응식
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][C:18]=1[O:19][CH3:20])[N:15]=[CH:14][N:13]=[C:12]2Cl)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:22][C:23]1[C:31]([OH:32])=[CH:30][CH:29]=[C:28]2[C:24]=1[CH:25]=[C:26]([CH3:33])[NH:27]2.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][C:18]=1[O:19][CH3:20])[N:15]=[CH:14][N:13]=[C:12]2[O:32][C:31]1[C:23]([F:22])=[C:24]2[C:28](=[CH:29][CH:30]=1)[NH:27][C:26]([CH3:33])=[CH:25]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

5

반응물 3

HCID 10796Cesium carbonateHCID 103520364-fluoro-2-methyl-1H-indol-5-olHCID 114265806-(Benzyloxy)-4-chloro-7-methoxyquinazoline

생성물 1

HCID 666463136-Benzyloxy-4-(4-fluoro-2-methylindol-5-yloxy)-7-methoxyquinazoline수율 38.2%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

A solution of 6-benzyloxy-4-chloro-7-methoxyquinazoline (0.39 g, 1.3 mmol), (EP1153920 production examples 28-30), 4-fluoro-5-hydroxy-2-methylindole (0.24 g, 1.43 mmol) and cesium carbonate (1.2 g, 4 mmol) in DMF (4 ml) was stirred at 95° C. for 45 minutes. After cooling, the mixture was filtered and the filtrate was evaporated under vacuum The residue was purified by column chromatography eluting with increasingly polar mixtures of methylene chloride and ethyl acetate to give 6-benzyloxy-4-(4-fluoro-2-methylindol-5-yloxy)-7-methoxyquinazoline (0.213 g, 37%).

후처리

  1. temperatureAfter cooling
  2. filtrationthe mixture was filtered
  3. customthe filtrate was evaporated under vacuum The residue
  4. customwas purified by column chromatography
  5. washeluting
  6. temperaturewith increasingly polar mixtures of methylene chloride and ethyl acetate

출처 및 근거

ORD 기록
ord-a2afab915d5d4541a23beb953c17a7f4
출처 데이터셋
uspto-grants-2007_09
특허 번호
US07268230B2

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