Chlorosuccinimide → 3-Chloro-6-fluoro-[1,2,4]triazolo[4,3-a]pyridine

HRID 630723Notes

Reaction equation

HRID 630723 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[N:9][N:10]=2)[CH:7]=1.[Cl:11]N1C(=O)CCC1=O>C(Cl)(Cl)Cl>[Cl:11][C:8]1[N:6]2[CH:7]=[C:2]([F:1])[CH:3]=[CH:4][C:5]2=[N:10][N:9]=1

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 552672456-Fluoro-[1,2,4]triazolo[4,3-a]pyridine

Product 1

HCID 552675403-Chloro-6-fluoro-[1,2,4]triazolo[4,3-a]pyridineYield 76%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of Intermediate 24a (789 mg, 5.98 mmol) and N-chlorosuccinimide (878 mg, 6.57 mmol) in chloroform (15 mL) was heated at 65° C. overnight. The cooled mixture was washed with sat. aq. NaHCO3 solution (2×15 mL) and dried (Na2SO4). The solvent was evaporated, then the residue suspended in diethyl ether (10 mL) and filtered to give the title compound (730 mg, 76%). LCMS (Method 1): Rt 1.83 min, m/z 172 [MH+].

Workup

  1. washThe cooled mixture was washed with sat. aq. NaHCO3 solution (2×15 mL)
  2. dry with materialdried (Na2SO4)
  3. customThe solvent was evaporated
  4. filtrationfiltered

Sources & evidence

ORD record
ord-35663f74f5f44670bdaa2e233fd9931c
Source dataset
uspto-grants-2016_04
Patent number
US09315503B2

Reaction notes

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