Potassium Carbonate → 7-Benzyloxy-4-(2,3-dimethylindol-5-yloxy)-6-methoxyquinazoline

HRID 454157

반응식

HRID 454157 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+].[CH3:28][C:29]1[NH:30][C:31]2[C:36]([C:37]=1[CH3:38])=[CH:35][C:34]([OH:39])=[CH:33][CH:32]=2>CN(C=O)C>[CH2:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13]([O:39][C:34]3[CH:35]=[C:36]4[C:31](=[CH:32][CH:33]=3)[NH:30][C:29]([CH3:28])=[C:37]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 106619987-(Benzyloxy)-4-chloro-6-methoxyquinazolineHCID 220307882,3-Dimethyl-1H-indol-5-ol

생성물 1

HCID 220308297-Benzyloxy-4-(2,3-dimethylindol-5-yloxy)-6-methoxyquinazoline수율 46%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
100 °C

실험 절차

A mixture of 7-benzyloxy-4-chloro-6-methoxyquinazoline (1.5 g, 4.99 mmol), (prepared as described for the starting material in Example 1), potassium carbonate (2.07 g, 15 mmol) and 2,3-dimethyl-5-hydroxyindole (1.21 g, 7.5 mmol), (Arch. Pharm. 1972, 305, 159), in DMF (75 ml) was stirred at 100° C. for 2 hours and allowed to cool to ambient temperature. The reaction mixture was filtered and the filtrate evaporated. The solid residue was purified by silica column chromatography, eluting with 2.5% methanol in dichoromethane to give 7-benzyloxy-4-(2,3-dimethylindol-5-yloxy)-6-methoxyquinazoline (976 mg, 46%).

후처리

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

출처 및 근거

ORD 기록
ord-12b150cc5e25498fae6c5565cf294aaa
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08492560B2

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