1,1'-Carbonyldiimidazole → 5-Trifluoromethyl-3-(4-chloro-2-thenoyl)-2-oxindole-1-carboxamide

HRID 486155Notes

Reaction equation

HRID 486155 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:7]([OH:9])=O)[S:5][CH:6]=1.C(N1C=CN=C1)(N1C=CN=C1)=O.[F:22][C:23]([F:38])([F:37])[C:24]1[CH:25]=[C:26]2[C:30](=[CH:31][CH:32]=1)[N:29]([C:33]([NH2:35])=[O:34])[C:28](=[O:36])[CH2:27]2>CN(C1C=CN=CC=1)C>[F:38][C:23]([F:22])([F:37])[C:24]1[CH:25]=[C:26]2[C:30](=[CH:31][CH:32]=1)[N:29]([C:33]([NH2:35])=[O:34])[C:28](=[O:36])[CH:27]2[C:7](=[O:9])[C:4]1[S:5][CH:6]=[C:2]([Cl:1])[CH:3]=1

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 122906954-Chlorothiophene-2-carboxylic acidHCID 136476291h-Indole-1-carboxamide,2,3-dihydro-2-oxo-5-(trifluoromethyl)-

Product 1

HCID 99083535-Trifluoromethyl-3-(4-chloro-2-thenoyl)-2-oxindole-1-carboxamideYield 82%

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Procedure

The experimental procedure used to produce the title compound was adopted from Example 55. A 388 mg (2.39 mmole) sample of 4-chloro-2-thiophenecarboxylic acid (prepared according to Iriarte, J., et al., J. Het. Chem., 13, 393 (1976)) was transformed into the acyl imidazole by reaction with 420 mg (2.59 mmole) of 1,1'-carbonyldiimidazole. The intermediate 4-chloro-2-thiophene-(1-imidazo)carboxamide coupled directly with 486 mg (1.99 mmole) of 5-trifluoromethyl-2-oxindole-1-carboxamide in the presence of 657 mg (5.37 mmole) of 4-(N,N-dimethylamino)pyridine to give 634 mg (1.63 mmole, 82%) of the title compound as a yellow solid m.p. 164°-6° C.

Sources & evidence

ORD record
ord-23974a3093c74d1abe208e0b1d95bb31
Source dataset
uspto-grants-1994_03
Patent number
US05290802

Reaction notes

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