1,1'-Carbonyldiimidazole → 1-(3,5-Dibromo-4-methylphenylcarbamoyl)-5-methoxy-6-trifluoromethylindoline

HRID 1977733Notes

Reaction equation

HRID 1977733 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:6]=[C:7]([Br:10])[C:8]=1[CH3:9])[NH2:5].[C:11]([N:18]1[CH:22]=[CH:21]N=[CH:19]1)(N1C=CN=C1)=[O:12].[CH3:23][O:24][C:25]1[CH:26]=[C:27]2C(=[CH:32][C:33]=1[C:34]([F:37])([F:36])[F:35])NCC2>>[Br:1][C:2]1[CH:3]=[C:4]([NH:5][C:11]([N:18]2[C:19]3[C:27](=[CH:26][C:25]([O:24][CH3:23])=[C:33]([C:34]([F:36])([F:37])[F:35])[CH:32]=3)[CH2:21][CH2:22]2)=[O:12])[CH:6]=[C:7]([Br:10])[C:8]=1[CH3:9]

Participants

4

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 70157793,5-Dibromo-4-methylanilineHCID 112067135-Methoxy-6-(trifluoromethyl)indoline

Product 1

HCID 180050891-(3,5-Dibromo-4-methylphenylcarbamoyl)-5-methoxy-6-trifluoromethylindolineYield 52%

Procedure

The title compound was prepared by the method of Example 1, from 3,5-dibromo-4-methylaniline (2.64 g, 10 mmol), 1,1′-carbonyldiimidazole (1.64 g, 10 mmol) and 5-methoxy-6-trifluoromethylindoline (D11) (2.2 g, 10 mmol). Crude product was recrystallised from DMSO/water and washed with methanol and ether, to give the title compound (2.64 g, 52%), mp>250° C.

Workup

  1. customCrude product was recrystallised from DMSO/water
  2. washwashed with methanol and ether

Sources & evidence

ORD record
ord-24316e4470b842b1ab8d33b0d0d66034
Source dataset
uspto-grants-2001_05
Patent number
US06235758B1

Reaction notes

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