Pyridine → N-(5-bromo[1,2,4]triazolo[1,5-a]pyridin-2-yl)benzamide

HRID 2382776Notes

Reaction equation

HRID 2382776 reaction equation
[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:10][C:11]1[N:16]2[N:17]=[C:18]([NH2:20])[N:19]=[C:15]2[CH:14]=[CH:13][CH:12]=1.N1C=CC=CC=1.C(OCC)C>C(Cl)Cl>[Br:10][C:11]1[N:16]2[N:17]=[C:18]([NH:20][C:1](=[O:8])[C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[N:19]=[C:15]2[CH:14]=[CH:13][CH:12]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 3283Diethyl EtherHCID 7412Benzoyl chlorideHCID 252159395-Bromo-[1,2,4]triazolo[1,5-a]pyridin-2-amine

Product 1

HCID 25212513N-(5-bromo[1,2,4]triazolo[1,5-a]pyridin-2-yl)benzamideYield 99.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Benzoyl chloride (4.40 g; 31.4 mmol; 2.0 eq.) was added to a suspension of 5-bromo[1,2,4]triazolo[1,5-a]pyridin-2-amine ((A3), 3.34 g; 15.7 mmol; 1.0 eq.) in pyridine (2.53 mL; 31.4 mmol; 2.0 eq.) and DCM (60 mL). The reaction mixture was then heated at reflux for 4 hours, after which it was cooled down to rt. Diethyl ether was added to the reaction mixture and the solid which precipitated was filtered off. The precipitate was resuspended in an aqueous mixture (pH 4/5), filtered and dried under vacuum to give the title compound as a white powder (4.97 g, quant. yield). HPLC, Rt: 2.40 min. (purity 93.4%), LC/MS, M+(ESI): 317.1, M−(ESI): 315.1.

Workup

  1. temperatureThe reaction mixture was then heated
  2. temperatureat reflux for 4 hours
  3. customthe solid which precipitated
  4. filtrationwas filtered off
  5. filtrationfiltered
  6. customdried under vacuum

Sources & evidence

ORD record
ord-66936c3beed74391a5e481df136eb765
Source dataset
uspto-grants-2012_09
Patent number
US08263595B2

Reaction notes

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