Potassium Carbonate → 7-Benzyloxy-4-(2-methylindol-5-yloxy)quinazoline

HRID 454086ノート

反応式

HRID 454086 の反応式
[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][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH:20][C:21]1[CH:22]=[C:23]2[C:27](=[CH:28][CH:29]=1)[NH:26][C:25]([CH3:30])=[CH:24]2.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH2:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13]([O:20][C:21]3[CH:22]=[C:23]4[C:27](=[CH:28][CH:29]=3)[NH:26][C:25]([CH3:30])=[CH:24]4)=[N:14][CH:15]=[N:16]2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 833362-methyl-1H-indol-5-olHCID 220309237-(Benzyloxy)-4-chloroquinazoline

生成物 1

HCID 220307817-Benzyloxy-4-(2-methylindol-5-yloxy)quinazoline収率 81%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
80 °C

実験手順

A solution of 7-benzyloxy-4-chloroquinazoline (2 g, 7.4 mmol), 5-hydroxy-2-methylindole (1.3 g, 8.9 mmol), (prepared as described for the starting material in Example 48), in DMF (20 ml) containing potassium carbonate (1.53 g, 11.1 mmol) was stirred at 80° C. for 3 hours. After cooling, the mixture was poured in portions into ice/water. The precipitate was filtered and washed with water and dried under vacuum. The solid was dissolved in methylene chloride and was purified by column chromatography eluting with ethyl acetate and methylene chloride (1/1) to give 7-benzyloxy-4-(2-methylindol-5-yloxy)quinazoline (2.28 g, 81%).

後処理

  1. temperatureAfter cooling
  2. filtrationThe precipitate was filtered
  3. washwashed with water
  4. customdried under vacuum
  5. dissolutionThe solid was dissolved in methylene chloride
  6. customwas purified by column chromatography
  7. washeluting with ethyl acetate and methylene chloride (1/1)

出典と根拠

ORDレコード
ord-c52c142e03e547ba86b371fdd85500f7
出典データセット
uspto-grants-2013_07
特許番号
US08492560B2

反応ノート

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