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

HRID 572102Notes

Reaction equation

HRID 572102 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[C:24]([Cl:25])=[CH:23][CH:22]=[CH:21][C:20]=2[Cl:26])=[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:26][C:20]1[CH:21]=[CH:22][CH:23]=[C:24]([Cl:25])[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 866867142,6-Dichloro-benzoic acid N'-(5-fluoro-pyridin-2-yl)-hydrazide

Product 1

HCID 848195623-(2,6-Dichlorophenyl)-6-fluoro-[1,2,4]triazolo[4,3-a]pyridineYield 93%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Hexachloroethane (2.60 g, 11.0 mmol) was added portionwise over 5 min at RT to a stirred mixture of Intermediate 26b (1.65 g, 5.50 mmol), triphenylphosphine (2.88 g, 11.0 mmol), and triethylamine (3.06 mL, 22.0 mmol) in THF (50 mL). The reaction mixture was stirred at RT for 18 h and then allowed to stand at RT for 72 h. The resulting suspension was filtered and the filtrate was concentrated in vacuo and 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 (1.44 g, 93%) as a beige solid. LCMS (Method 3): Rt 3.08 min, m/z 282, 284 [MH+].

Workup

  1. waitto stand at RT for 72 h
  2. filtrationThe resulting suspension was filtered
  3. concentrationthe filtrate was concentrated in vacuo
  4. custompurified by FCC
  5. washThe cartridge was washed with MeOH
  6. washthe product was eluted with 2M NH3 in MeOH

Sources & evidence

ORD record
ord-b04b57a778874fc8bac43ee8bd670add
Source dataset
uspto-grants-2015_05
Patent number
US09029373B2

Reaction notes

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