1,1'-Carbonyldiimidazole → 6-Chloro-3-(5-bromo-3-furoyl)-2-oxindole-1-carboxamide

HRID 486158Notes

Reaction equation

HRID 486158 reaction equation
[Br:1][C:2]1[O:6][CH:5]=[C:4]([C:7]([OH:9])=O)[CH:3]=1.C(N1C=CN=C1)(N1C=CN=C1)=O.[Cl:22][C:23]1[CH:31]=[C:30]2[C:26]([CH2:27][C:28](=[O:35])[N:29]2[C:32]([NH2:34])=[O:33])=[CH:25][CH:24]=1>CN(C1C=CN=CC=1)C.C(O)(=O)C>[Cl:22][C:23]1[CH:31]=[C:30]2[C:26]([CH:27]([C:7]([C:4]3[CH:3]=[C:2]([Br:1])[O:6][CH:5]=3)=[O:9])[C:28](=[O:35])[N:29]2[C:32]([NH2:34])=[O:33])=[CH:25][CH:24]=1

Participants

6

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 133335605-Bromofuran-3-carboxylic acidHCID 136476276-Chloro-2-oxindole-1-carboxamide

Product 1

HCID 98214086-Chloro-3-(5-bromo-3-furoyl)-2-oxindole-1-carboxamideYield 11%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 176Acetic AcidSolvent

Procedure

The experimental procedure used to produce the title compound was adopted from Example 55. A 750 mg (3.93 mmole) portion of 5-bromo-3-furoic acid (prepared according to Amaral, L., et al., J.O.C., 41, 2350 (1976)) was transformed into the acyl imidazole by reaction with 690 mg (4.25 mmole) of 1,1'-carbonyldiimidazole. The intermediate 5-bromo-3-furan-(1-imidazo)carboxamide coupled directly with 689 mg (3.27 mmole) of 6-chloro-2-oxindole-1-carboxamide in the presence of 1.08 g (8.83 mmole) of 4-(N,N-dimethylamino)pyridine to give 500 mg (40% yield) of crude greenish-yellow solid. Recrystallization gave 143 mg (0.37 mmole, 11% yield) of pure title compound as a greenish solid, m.p. 232°-4° C. (acetic acid).

Workup

  1. customto give 500 mg (40% yield) of crude greenish-yellow solid
  2. customRecrystallization

Sources & evidence

ORD record
ord-6222cc16fc41447381bf50679bbb8668
Source dataset
uspto-grants-1994_03
Patent number
US05290802

Reaction notes

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