Potassium Carbonate → 7-(Benzyloxy)-4-((4-fluoro-2-methyl-1H-indol-5-yl)oxy)-6-methoxyquinazoline

HRID 2068044노트

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HRID 2068044 반응식
[CH2:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13](Cl)=[N:14][CH:15]=[N:16]2)=[CH:11][C:10]=1[O:20][CH3:21])[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-].[K+].[K+]>CN1C(=O)CCC1>[CH2:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13]([O:32][C:31]3[C:23]([F:22])=[C:24]4[C:28](=[CH:29][CH:30]=3)[NH:27][C:26]([CH3:33])=[CH:25]4)=[N:14][CH:15]=[N:16]2)=[CH:11][C:10]=1[O:20][CH3:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 103520364-fluoro-2-methyl-1H-indol-5-olHCID 106619987-(Benzyloxy)-4-chloro-6-methoxyquinazoline

생성물 1

HCID 101512047-(Benzyloxy)-4-((4-fluoro-2-methyl-1H-indol-5-yl)oxy)-6-methoxyquinazoline수율 57.5%

시약·촉매·용매 1

HCID 13387N-methyl-2-pyrrolidone용매

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온도
95 °C

실험 절차

A suspension of 7-benzyloxy-4-chloro-6-methoxyquinazoline free base (10 g, 33.2 mmol), 4-fluoro-5-hydroxy-2-methylindole (5.9 g, 35.7 mmol), (prepared as described for the starting material in Example 1), and potassium carbonate (9.2 g, 66.6 mmol) in NMP (100 ml) was stirred at 95° C. for 1 hour. After cooling, the mixture was partitioned between ethyl acetate and aqueous sodium hydrogen carbonate. The organic layer was separated, washed with brine and dried over magnesium sulphate and evaporated under vacuum. The residue was triturated under acetonitrile and the suspension was cooled. The precipitate was filtered and dried under vacuum to give 7-benzyloxy-4-(4-fluoro-2-methylindol-5-yloxy)-6-methoxyquinazoline (8.2 g, 57%).

후처리

  1. custom(prepared
  2. temperatureAfter cooling
  3. customthe mixture was partitioned between ethyl acetate and aqueous sodium hydrogen carbonate
  4. customThe organic layer was separated
  5. washwashed with brine
  6. dry with materialdried over magnesium sulphate
  7. customevaporated under vacuum
  8. customThe residue was triturated under acetonitrile
  9. temperaturethe suspension was cooled
  10. filtrationThe precipitate was filtered
  11. customdried under vacuum

출처 및 근거

ORD 기록
ord-f5d81843921c4a8db09ddaac8e54c446
출처 데이터셋
uspto-grants-2012_10
특허 번호
US08293902B2

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