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

HRID 75612Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 75612
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

Komponenten

6

Edukt 4

HCID 6214HexachloroethaneHCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 866867142,6-Dichloro-benzoic acid N'-(5-fluoro-pyridin-2-yl)-hydrazide

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

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+].

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-3fd6aa7e21954ccb94b8bd7b645f2230
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08835431B2

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