4-Bromophenol → 7-(4-Bromo-phenoxy)-2-furan-2-yl-[1,2,4]triazolo[1,5-a]pyridin-5-ylamine

HRID 277086Notes

Reaction equation

HRID 277086 reaction equation
Br[C:2]1[CH:7]=[C:6]([NH2:8])[N:5]2[N:9]=[C:10]([C:12]3[O:13][CH:14]=[CH:15][CH:16]=3)[N:11]=[C:4]2[CH:3]=1.[Br:17][C:18]1[CH:23]=[CH:22][C:21]([OH:24])=[CH:20][CH:19]=1>CN1CCCC1=O>[Br:17][C:18]1[CH:23]=[CH:22][C:21]([O:24][C:2]2[CH:7]=[C:6]([NH2:8])[N:5]3[N:9]=[C:10]([C:12]4[O:13][CH:14]=[CH:15][CH:16]=4)[N:11]=[C:4]3[CH:3]=2)=[CH:20][CH:19]=1

Participants

4

Reactant 2

HCID 78084-BromophenolHCID 111967207-Bromo-2-furan-2-yl-[1,2,4]triazolo[1,5-a]pyridin-5-ylamine

Product 1

HCID 183136147-(4-Bromo-phenoxy)-2-furan-2-yl-[1,2,4]triazolo[1,5-a]pyridin-5-ylamine

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A mixture of 1 eq. 7-bromo-2-furan-2-yl-[1,2,4]triazolo[1,5-a]pyridin-5-ylamine, 5 eq. p-bromo-phenol and a catalytic amount of CS2CO3 in 200 μl N-methyl-pyrrolidon was heated for 2 h to 160°. The mixture was, after filtration, purified with reversed phase column chromatography eluting with an acetonitrile/water gradient yielding the title compound, MS m/e (%): 371 M+ (100%).

Workup

  1. additionA mixture of 1 eq
  2. filtrationafter filtration
  3. custompurified with reversed phase column chromatography
  4. washeluting with an acetonitrile/water

Sources & evidence

ORD record
ord-00b1fd2f0e7d463b9cc7932ce47b8466
Source dataset
uspto-grants-2002_03
Patent number
US06355653B1

Reaction notes

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