2-Amino-5-bromopyridine → Benzamide, N-(((5-bromo-2-pyridinyl)amino)carbonyl)-2,6-difluoro-

HRID 1758928Notes

Reaction equation

HRID 1758928 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([NH2:8])=[N:6][CH:7]=1.[F:9][C:10]1[CH:20]=[CH:19][CH:18]=[C:17]([F:21])[C:11]=1[C:12]([N:14]=[C:15]=[O:16])=[O:13]>C(OCC)(=O)C>[F:9][C:10]1[CH:20]=[CH:19][CH:18]=[C:17]([F:21])[C:11]=1[C:12]([NH:14][C:15]([NH:8][C:5]1[CH:4]=[CH:3][C:2]([Br:1])=[CH:7][N:6]=1)=[O:16])=[O:13]

Participants

4

Reactant 2

HCID 706222-Amino-5-bromopyridineHCID 27333692,6-Difluorobenzoyl isocyanate

Product 1

HCID 326531Benzamide, N-(((5-bromo-2-pyridinyl)amino)carbonyl)-2,6-difluoro-

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A 2 g. portion of 5-bromo-2-aminopyridine was reacted with 2.5 g. of 2,6-difluorobenzoyl isocyanate under nitrogen in 50 ml. of ethyl acetate. The reaction mixture was stirred for 3 days, and was then filtered. The solids were washed with dichloromethane, ethyl acetate and diethyl ether and dried under vacuum to obtain the desired product, m.p. 232°-235° C. The elemental analysis showed:

Workup

  1. filtrationwas then filtered
  2. washThe solids were washed with dichloromethane, ethyl acetate and diethyl ether
  3. customdried under vacuum

Sources & evidence

ORD record
ord-9e652bc170f64f8eb8b8890270133c15
Source dataset
uspto-grants-1982_07
Patent number
US04338321

Reaction notes

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