Hexachloroethane → 3-(2-Chlorophenyl)-6-fluoro-[1,2,4]triazolo[4,3-a]pyridine

HRID 75617Notes

Reaction equation

HRID 75617 reaction equation
ClC(Cl)(Cl)C(Cl)(Cl)Cl.[F:9][C:10]1[CH:11]=[CH:12][C:13]([NH:16][NH:17][C:18](=O)[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[Cl:25])=[N:14][CH:15]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(N(CC)CC)C>C1COCC1>[Cl:25][C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=1[C:18]1[N:14]2[CH:15]=[C:10]([F:9])[CH:11]=[CH:12][C:13]2=[N:16][N:17]=1

Participants

6

Reactant 4

HCID 6214HexachloroethaneHCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 866867222-Chloro-benzoic acid N'-(5-fluoro-pyridin-2-yl)-hydrazide

Product 1

HCID 848195603-(2-Chlorophenyl)-6-fluoro-[1,2,4]triazolo[4,3-a]pyridineYield 99.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Hexachloroethane (3.47 g, 14.68 mmol) was added portionwise at RT to a stirred mixture of Intermediate 31a (1.95 g, 7.34 mmol), triphenylphosphine (3.85 g, 14.68 mmol), and triethylamine (4.12 mL, 29.36 mmol) in anhydrous THF (60 mL). The reaction mixture was stirred at RT for 3.5 h. The resulting suspension was filtered, washing the solid with Et2O. The filtrate was concentrated in vacuo and the resultant residue purified by FCC using SCX-2 cartridge. The cartridge was washed with MeOH and the product was eluted with 2M NH3 in MeOH to give the title compound (1.81 g, quantitative) as a fawn coloured solid. LCMS (Method 3): Rt 2.96 min, m/z 248 [MH+].

Workup

  1. filtrationThe resulting suspension was filtered
  2. washwashing the solid with Et2O
  3. concentrationThe filtrate was concentrated in vacuo
  4. customthe resultant residue purified by FCC
  5. washThe cartridge was washed with MeOH
  6. washthe product was eluted with 2M NH3 in MeOH

Sources & evidence

ORD record
ord-e22244776e62412fa89e32bdb800990d
Source dataset
uspto-grants-2014_09
Patent number
US08835431B2

Reaction notes

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