2-Chlorobenzoyl chloride → 7-Bromo-3-(2-chlorophenyl)-[1,2,4]triazolo[4,3-a]pyridine

HRID 643671Notes

Reaction equation

HRID 643671 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([NH:8][NH2:9])[CH:3]=1.[Cl:10][C:11]1[CH:19]=[CH:18][CH:17]=[CH:16][C:12]=1[C:13](Cl)=O>CO>[Br:1][C:2]1[CH:7]=[CH:6][N:5]2[C:13]([C:12]3[CH:16]=[CH:17][CH:18]=[CH:19][C:11]=3[Cl:10])=[N:9][N:8]=[C:4]2[CH:3]=1

Participants

4

Reactant 2

HCID 691102-Chlorobenzoyl chlorideHCID 534028634-Bromo-2-hydrazinylpyridine

Product 1

HCID 592613697-Bromo-3-(2-chlorophenyl)-[1,2,4]triazolo[4,3-a]pyridine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
115 °C

Procedure

A mixture of 1-(4-bromopyridin-2-yl)hydrazine (1.00 g, 5.3 mmol) and 2-chlorobenzoyl chloride (8.00 ml, 63 mmol, Aldrich) was heated to 115° C. for 3 h. The mixture was diluted with MeOH and concentrated over SiO2. The residue was purified using column chromatography (MeOH/CH2Cl2=0-10%) yielding the title compound as a tan solid. MS (ESI, pos. ion) m/z: 264.0 (M+1).

Workup

  1. concentrationconcentrated over SiO2
  2. customThe residue was purified

Sources & evidence

ORD record
ord-b13c72e7b41f4f72893123222bbaa41a
Source dataset
uspto-grants-2010_04
Patent number
US07700593B2

Reaction notes

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