2-Thiophenecarbonyl chloride → Thiophene-2-carboxylic acid [4-(2-oxo-2,3-dihydro-1H-indole-6-carbonyl)-phenyl]-amide

HRID 640855Notes

Reaction equation

HRID 640855 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:27]=[CH:26][C:13]([C:14]([C:16]2[CH:24]=[C:23]3[C:19]([CH2:20][C:21](=[O:25])[NH:22]3)=[CH:18][CH:17]=2)=[O:15])=[CH:12][CH:11]=1>C1COCC1>[O:25]=[C:21]1[CH2:20][C:19]2[C:23](=[CH:24][C:16]([C:14]([C:13]3[CH:12]=[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]=3)=[O:15])=[CH:17][CH:18]=2)[NH:22]1

Participants

4

Reactant 2

HCID 789282-Thiophenecarbonyl chlorideHCID 592564856-(4-Amino-benzoyl)-1,3-dihydro-indol-2-one

Product 1

HCID 86610381Thiophene-2-carboxylic acid [4-(2-oxo-2,3-dihydro-1H-indole-6-carbonyl)-phenyl]-amideYield 64%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A dry 25 mL flask was charged with Thiophene-2-carbonyl chloride (0.756 g, 5.16 mmol) and THF (10 mL). 6-(4-Amino-benzoyl)-1,3-dihydro-indol-2-one (as prepared in Example 15, 1.02 g, 3.98 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, and the crude residue was dissolved in EtOH (5 mL). The ethanolic solution was treated with 1M NaOH(aq) (2 mL) and stirred for 30 min. The basic solution was acidified to a pH of 1 with 1M HCl(aq) yielding a tan precipitate. The tan solids were filtered to afford the pure Thiophene-2-carboxylic acid [4-(2-oxo-2,3-dihydro-1H-indole-6-carbonyl)-phenyl]-amide (0.924 g, 2.53 mmol, 64%).

Workup

  1. temperatureto reflux for 3 h
  2. customThe room temperature reaction mixture
  3. concentrationwas concentrated in vacuo
  4. dissolutionthe crude residue was dissolved in EtOH (5 mL)
  5. additionThe ethanolic solution was treated with 1M NaOH(aq) (2 mL)
  6. customyielding a tan precipitate
  7. filtrationThe tan solids were filtered

Sources & evidence

ORD record
ord-6047e8bd5a214222b4389b697262aa38
Source dataset
uspto-grants-2010_04
Patent number
US07692005B2

Reaction notes

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