1,1'-Carbonyldiimidazole → 5-Chloro-3-(5-bromo-3-thenoyl)-2-oxindole-1-carboxamide

HRID 1463507Notes

Reaction equation

HRID 1463507 reaction equation
[Br:1][C:2]1[S:6][CH:5]=[C:4]([C:7]([OH:9])=O)[CH:3]=1.C(N1C=CN=C1)(N1C=CN=C1)=O.[N-]1C=CN=C1.[Cl:27][C:28]1[CH:29]=[C:30]2[C:34](=[CH:35][CH:36]=1)[N:33]([C:37]([NH2:39])=[O:38])[C:32](=[O:40])[CH2:31]2>CN(C)C=O.CN(C1C=CN=CC=1)C>[Cl:27][C:28]1[CH:29]=[C:30]2[C:34](=[CH:35][CH:36]=1)[N:33]([C:37]([NH2:39])=[O:38])[C:32](=[O:40])[CH:31]2[C:7](=[O:9])[C:4]1[CH:3]=[C:2]([Br:1])[S:6][CH:5]=1

Participants

7

Reactant 4

HCID 682631,1'-CarbonyldiimidazoleHCID 3386966ImidazolateHCID 98591595-Chloro-2-oxo-2,3-dihydro-1H-indole-1-carboxamideHCID 120399785-Bromothiophene-3-carboxylic acid

Product 1

HCID 702216865-Chloro-3-(5-bromo-3-thenoyl)-2-oxindole-1-carboxamide

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

The title compound was prepared according to the procedure of Example 55. A 1.00 g (4.83 mmole) portion of 5-bromo-3-thiophenecarboxylic acid (prepared as described in J. Am. Chem. Soc., 76, 2445 (1954)) was combined with 848 mg (5.23 mmole) of 1,1'-carbonyldiimidazole in 5 ml of N,N-dimethylformamide and the intermediate imidazolide coupled directly with 848 mg (4.02 mmole) of 5-chloro-2-oxindole-1-carboxamide in the presence of 1.33 g (10.89 mmole) of 4-(N,N-dimethylamino)pyridine. The resulting crude green product (1.22 g, 76% yield) was recrystallized to furnish 540 mg (1.35 mmole, 34% yield) of yellow solid, m.p. 238°-40° C. (acetic acid).

Sources & evidence

ORD record
ord-d7e203e6b3c24504ab801cdf9919f0d3
Source dataset
uspto-grants-1994_04
Patent number
US05300655

Reaction notes

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