Tetrahydrofuran → 4-bromo-N-[4,6-dibromo-2-(hydrazinocarbonyl)phenyl]-1-(3-chloro-2-pyridinyl)-1H-pyrrole-2-carboxamide

HRID 252007Notes

Reaction equation

HRID 252007 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([Br:26])[C:5]2[N:10]=[C:9]([C:11]3[N:12]([C:17]4[C:22]([Cl:23])=[CH:21][CH:20]=[CH:19][N:18]=4)[CH:13]=[C:14]([Br:16])[CH:15]=3)[O:8][C:7](=[O:24])[C:6]=2[CH:25]=1.O.[NH2:28][NH2:29].O1CCCC1>O>[Br:16][C:14]1[CH:15]=[C:11]([C:9]([NH:10][C:5]2[C:4]([Br:26])=[CH:3][C:2]([Br:1])=[CH:25][C:6]=2[C:7]([NH:28][NH2:29])=[O:24])=[O:8])[N:12]([C:17]2[C:22]([Cl:23])=[CH:21][CH:20]=[CH:19][N:18]=2)[CH:13]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 24654Hydrazine hydrate (1:1)HCID 668541976,8-dibromo-2-[4-bromo-1-(3-chloro-2-pyridinyl)-1H-pyrrol-2-yl]-4H-3,1-benzoxazine-4-one

Product 1

HCID 668538934-bromo-N-[4,6-dibromo-2-(hydrazinocarbonyl)phenyl]-1-(3-chloro-2-pyridinyl)-1H-pyrrole-2-carboxamideYield 88.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Under ice-cooling, 0.569 g of 6,8-dibromo-2-[4-bromo-1-(3-chloro-2-pyridinyl)-1H-pyrrol-2-yl]-4H-3,1-benzoxazine-4-one, 0.20 g of hydrazine monohydrate and 2 ml of tetrahydrofuran were mixed, and the mixture was stirred at room temperature for 1 hour. Water was poured into the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with water, dried over sodium sulfate, and concentrated under reduced pressure to obtain 0.53 g of 4-bromo-N-[4,6-dibromo-2-(hydrazinocarbonyl)phenyl]-1-(3-chloro-2-pyridinyl)-1H-pyrrole-2-carboxamide of the formula:

Workup

  1. temperatureUnder ice-cooling
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with water
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-431ba141a17e4862a05cfa1de1ac1ebf
Source dataset
uspto-grants-2011_01
Patent number
US07867949B2

Reaction notes

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