5-Bromo-2-furanecarboxylic acid → N-[(3-Chloro-5-trifluoromethyl-2-pyridyl)methyl]-5-bromofuramide

HRID 987000Notes

Reaction equation

HRID 987000 reaction equation
[Br:1][C:2]1[O:6][C:5]([C:7]([OH:9])=O)=[CH:4][CH:3]=1.C(C1NC=CN=1)(C1NC=CN=1)=O.[Cl:22][C:23]1[C:24]([CH2:33][NH2:34])=[N:25][CH:26]=[C:27]([C:29]([F:32])([F:31])[F:30])[CH:28]=1>ClCCl>[Cl:22][C:23]1[C:24]([CH2:33][NH:34][C:7]([C:5]2[O:6][C:2]([Br:1])=[CH:3][CH:4]=2)=[O:9])=[N:25][CH:26]=[C:27]([C:29]([F:32])([F:30])[F:31])[CH:28]=1

Participants

5

Reactant 3

HCID 685115-Bromo-2-furanecarboxylic acidHCID 5250894Bis-(1H-imidazol-2-YL)-methanoneHCID 11085087(3-Chloro-5-(trifluoromethyl)pyridin-2-yl)methanamine

Product 1

HCID 22988183N-[(3-Chloro-5-trifluoromethyl-2-pyridyl)methyl]-5-bromofuramide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 5-bromofuroic acid (0.19 g) and carbonyl diimidazole (CDI) in dichloromethane was added (3-chloro-5-trifluoromethyl-2-pyridyl)methylamine and the mixture was stirred at room temperature overnight. The mixture was washed with 2M hydrochloric acid, then saturated sodium bicarbonate, dried (MgSO4) and evaporated to give the title product, m.p. 77.8° C.

Workup

  1. washThe mixture was washed with 2M hydrochloric acid
  2. dry with materialsaturated sodium bicarbonate, dried (MgSO4)
  3. customevaporated

Sources & evidence

ORD record
ord-7378f91fee044bb1bc0efdd366d028ff
Source dataset
uspto-grants-2003_10
Patent number
US06630495B1

Reaction notes

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