Potassium Carbonate → 7-Benzyloxy-6-methoxy-4-(3-methylindol-5-yloxy)quinazoline

HRID 454266

반응식

HRID 454266 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.C(=O)([O-])[O-].[K+].[K+].[OH:28][C:29]1[CH:30]=[C:31]2[C:35](=[CH:36][CH:37]=1)[NH:34][CH:33]=[C:32]2[CH3:38]>CC(N(C)C)=O>[CH2:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13]([O:28][C:29]3[CH:30]=[C:31]4[C:35](=[CH:36][CH:37]=3)[NH:34][CH:33]=[C:32]4[CH3:38])=[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 1927343-methyl-1H-indol-5-olHCID 106619987-(Benzyloxy)-4-chloro-6-methoxyquinazoline

생성물 1

HCID 220308717-Benzyloxy-6-methoxy-4-(3-methylindol-5-yloxy)quinazoline수율 73%

시약·촉매·용매 1

HCID 31374Dimethylacetamide용매

반응 조건

온도
75 °C

실험 절차

A mixture of 7-benzyloxy-4-chloro-6-methoxyquinazoline (7.859 g, 26.1 mmol), (prepared as described for the starting material in Example 1), potassium carbonate (18.03 g, 130 mmol) and 5-hydroxy-3-methylindole (5.00 g, 34.0 mmol), (Journal of Organic Chemistry 1993, 58, 3757), in DMA (600 ml) was stirred at 75° C. for 2 hours and allowed to cool to ambient temperature. The reaction mixture was filtered and the filtrate evaporated in vacuo. The crude solid was purified by silica column chromatography, eluting with 2.5% methanol/97.5% dichloromethane to give 7-benzyloxy-6-methoxy-4-(3-methylindol-5-yloxy)quinazoline (7.791 g, 73%).

후처리

  1. custom(prepared
  2. temperatureto cool to ambient temperature
  3. filtrationThe reaction mixture was filtered
  4. customthe filtrate evaporated in vacuo
  5. customThe crude solid was purified by silica column chromatography
  6. washeluting with 2.5% methanol/97.5% dichloromethane

출처 및 근거

ORD 기록
ord-19a6ba3247144ac1b953bebf18ab3864
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08492560B2

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