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

HRID 11426

Reaction equation

HRID 11426 reaction equation
[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]

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-798a65328c5e4ea19223cb360c86736d
Source dataset
uspto-grants-2006_08
Patent number
US07098240B2

Linked notes

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