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Potassium Carbonate → 4-(6-Fluoroindol-5-yloxy)-6-methoxy-7-(3-piperidinopropoxy)quinazoline

HRID 454243
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HRID 454243 반응식
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH2:15][CH2:16][CH2:17][N:18]3[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]3)=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][N:3]=1.[F:24][C:25]1[CH:33]=[C:32]2[C:28]([CH:29]=[CH:30][NH:31]2)=[CH:27][C:26]=1[OH:34].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[F:24][C:25]1[CH:33]=[C:32]2[C:28]([CH:29]=[CH:30][NH:31]2)=[CH:27][C:26]=1[O:34][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH2:15][CH2:16][CH2:17][N:18]3[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]3)=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][N:3]=1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 110021914-Chloro-6-methoxy-7-(3-(piperidin-1-YL)propoxy)quinazolineHCID 220309296-Fluoro-1H-indol-5-ol

생성물 1

HCID 220307274-(6-Fluoroindol-5-yloxy)-6-methoxy-7-(3-piperidinopropoxy)quinazoline수율 46.6%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
95 °C

실험 절차

A mixture of 4-chloro-6-methoxy-7-(3-piperidinopropoxy)quinazoline (222 mg, 0.662 mmol), (prepared as described for the starting material in Example 67), and 6-fluoro-5-hydroxyindole (120 mg, 0.794 mmol), (prepared as described for the starting material in Example 242), in DMF (3 ml) containing potassium carbonate (137 mg, 0.993 mmol) was heated at 95° C. for 3.5 hours. After cooling the mixture was poured onto water and extracted with ethyl acetate. The organic layers were washed with water, brine, dried (MgSO4) and evaporated. The residue was triturated with ether, filtered and dried under vacuum to give 4-(6-fluoroindol-5-yloxy)-6-methoxy-7-(3-piperidinopropoxy)quinazoline (139 mg, 46%).

후처리

  1. custom(prepared
  2. custom(prepared
  3. temperatureAfter cooling the mixture
  4. additionwas poured onto water
  5. extractionextracted with ethyl acetate
  6. washThe organic layers were washed with water, brine
  7. dry with materialdried (MgSO4)
  8. customevaporated
  9. customThe residue was triturated with ether
  10. filtrationfiltered
  11. customdried under vacuum

출처 및 근거

ORD 기록
ord-965ea7e2abd741b4ae10891c05457c61
출처 데이터셋
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08492560B2

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