(1-Benzothiophen-3-yl)boronic acid → (Aminocarbonyl)amino-5-(1-benzothien-3-yl)thiophene-2-carboxamide

HRID 11426

反応式

HRID 11426 の反応式
[NH2:1][C:2]([NH:4][C:5]1[CH:9]=[C:8](Br)[S:7][C:6]=1[C:11]([NH2:13])=[O:12])=[O:3].[S:14]1[C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=2[C:16](B(O)O)=[CH:15]1>COCCOC>[NH2:1][C:2]([NH:4][C:5]1[CH:9]=[C:8]([C:16]2[C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[S:14][CH:15]=2)[S:7][C:6]=1[C:11]([NH2:13])=[O:12])=[O:3]

参加物

4

反応物 2

HCID 2776344(1-Benzothiophen-3-yl)boronic acidHCID 219758555-Bromo-3-ureidothiophene-2-carboxamide

生成物 1

HCID 9836627(Aminocarbonyl)amino-5-(1-benzothien-3-yl)thiophene-2-carboxamide

試薬・触媒・溶媒 1

HCID 80711,2-Dimethoxyethane溶媒

実験手順

3-[(Aminocarbonyl)amino-5-bromothiophene-2-carboxamide (0.222 g) and 1-benzothien-3-ylboronic acid (0.449 g) were sonicated in 1,2-dimethoxyethane (15 ml) and saturated aqueous sodium hydrogen carbonate solution (3.5 ml) and purged with argon. Tetrakis(triphenylphosphine)-palladium (95 mg) was added and the mixture was heated at reflux with stirring for 4.5 h, then allowed to cool and stirred at room temperature overnight. The solution was filtered and washed through with 1,2-dimethoxyethane and water. The filtrate was concentrated in vacuo and taken up in dichloromethane (20 ml) and saturated aqueous sodium hydrogen carbonate solution (20 ml). The solid product was collected by filtration, washed with dichloromethane, water, diethyl ether and dried (226 mg).

後処理

  1. customsaturated aqueous sodium hydrogen carbonate solution (3.5 ml) and purged with argon
  2. additionTetrakis(triphenylphosphine)-palladium (95 mg) was added
  3. temperaturethe mixture was heated
  4. temperatureat reflux
  5. temperatureto cool
  6. stirringstirred at room temperature overnight
  7. filtrationThe solution was filtered
  8. washwashed through with 1,2-dimethoxyethane and water
  9. concentrationThe filtrate was concentrated in vacuo
  10. filtrationThe solid product was collected by filtration
  11. washwashed with dichloromethane, water, diethyl ether
  12. customdried (226 mg)

出典と根拠

ORDレコード
ord-798a65328c5e4ea19223cb360c86736d
出典データセット
uspto-grants-2006_08
特許番号
US07098240B2

関連ノート

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