2-Thiophenecarbonyl chloride → Thiophene-2-carboxylic acid [3-(2-oxo-2,3-dihydro-1H-indole-6-carbonyl)-phenyl]-amide

HRID 640890Notes

Reaction equation

HRID 640890 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6](Cl)=[O:7].[NH2:9][C:10]1[CH:11]=[C:12]([CH:25]=[CH:26][CH:27]=1)[C:13]([C:15]1[CH:23]=[C:22]2[C:18]([CH2:19][C:20](=[O:24])[NH:21]2)=[CH:17][CH:16]=1)=[O:14]>C1COCC1>[O:24]=[C:20]1[CH2:19][C:18]2[C:22](=[CH:23][C:15]([C:13]([C:12]3[CH:11]=[C:10]([NH:9][C:6]([C:2]4[S:1][CH:5]=[CH:4][CH:3]=4)=[O:7])[CH:27]=[CH:26][CH:25]=3)=[O:14])=[CH:16][CH:17]=2)[NH:21]1

Participants

4

Reactant 2

HCID 789282-Thiophenecarbonyl chlorideHCID 592564786-(3-Amino-benzoyl)-1,3-dihydro-indol-2-one

Product 1

HCID 86610387Thiophene-2-carboxylic acid [3-(2-oxo-2,3-dihydro-1H-indole-6-carbonyl)-phenyl]-amideYield 84%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A dry 250 mL flask was charged with Thiophene-2-carbonyl chloride (1.14 g, 7.77 mmol) and THF (60 mL). 6-(3-Amino-benzoyl)-1,3-dihydro-indol-2-one (as prepared in Example 40, 1.508 g, 5.978 mmol) was added to the THF solution of the acid chloride, and the mixture was allowed to reflux for 3 h. The reaction mixture was then allowed to cool to room temperature. The room temperature reaction mixture was concentrated in vacuo. The solid residue was suspended in boiling EtOAc. The suspension was allowed to cool to room temperature before filtering to afford the Thiophene-2-carboxylic acid [3-(2-oxo-2,3-dihydro-1H-indole-6-carbonyl)-phenyl]-amide as a tan solid (1.82 g, 5.02 mmol, 84%).

Workup

  1. temperatureto reflux for 3 h
  2. customThe room temperature reaction mixture
  3. concentrationwas concentrated in vacuo
  4. temperatureto cool to room temperature
  5. filtrationbefore filtering

Sources & evidence

ORD record
ord-c191d0ab587548069f0c993de6c35be6
Source dataset
uspto-grants-2010_04
Patent number
US07692005B2

Reaction notes

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