Dichloromethane → 6-((7-(4-chlorophenyl)-5-methyl-3-oxo-8-(pyridin-4-yl)-[1,2,4]triazolo[4,3-a]pyridine-2(3H)-yl)methyl)nicotinonitrile

HRID 2101384Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2101384
Br[C:2]1[C:3]2[N:4]([C:16](=[O:28])[N:17]([CH2:19][C:20]3[CH:27]=[CH:26][C:23]([C:24]#[N:25])=[CH:22][N:21]=3)[N:18]=2)[C:5]([CH3:15])=[CH:6][C:7]=1[C:8]1[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][CH:9]=1.CC1(C)C(C)(C)OB([C:37]2[CH:42]=[CH:41][N:40]=[CH:39][CH:38]=2)O1.ClCCl.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>C1COCC1>[Cl:14][C:11]1[CH:12]=[CH:13][C:8]([C:7]2[CH:6]=[C:5]([CH3:15])[N:4]3[C:16](=[O:28])[N:17]([CH2:19][C:20]4[CH:27]=[CH:26][C:23]([C:24]#[N:25])=[CH:22][N:21]=4)[N:18]=[C:3]3[C:2]=2[C:37]2[CH:42]=[CH:41][N:40]=[CH:39][CH:38]=2)=[CH:9][CH:10]=1

Komponenten

6

Edukt 4

HCID 6344DichloromethaneHCID 62657Potassium Phosphate, TribasicHCID 27346484-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridineHCID 577993886-((8-bromo-7-(4-chlorophenyl)-5-methyl-3-oxo-[1,2,4]triazolo[4,3-a]pyridine-2(3H)-yl)methyl)nicotinonitrile

Produkt 1

HCID 577994166-((7-(4-chlorophenyl)-5-methyl-3-oxo-8-(pyridin-4-yl)-[1,2,4]triazolo[4,3-a]pyridine-2(3H)-yl)methyl)nicotinonitrileAusbeute 62,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

In a pressure tube, to a stirring solution of 6-((8-bromo-7-(4-chlorophenyl)-5-methyl-3-oxo-[1,2,4]triazolo[4,3-a]pyridine-2(3H)-yl)methyl)nicotinonitrile (54 mg, 0.11 mmol) in THF (2 mL) at room temperature under argon was added 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (45 mg, 0.22 mmol), 1,1′-bis(diphenylphosphino)ferrocene palladium (II) chloride complex with dichloromethane (9 mg, 0.011 mmol) and powdered K3PO4 (60 mg, 0.28 mmol). The resulting suspension was stirred and heated at 100° C. under argon for 7 h. The reaction mixture was filtered through filter paper and the filtrate was concentrated under vacuum to a dark brown solid. The crude product thus obtained was purified by reverse phase preparative HPLC (without TFA) to obtain 31 mg of the title compound as a yellow solid. HPLC/MS: retention time=2.482 min, [M+H]+=453.

Aufarbeitung

  1. filtrationThe reaction mixture was filtered
  2. filtrationthrough filter paper
  3. concentrationthe filtrate was concentrated under vacuum to a dark brown solid
  4. customThe crude product thus obtained
  5. customwas purified by reverse phase preparative HPLC (without TFA)

Quellen und Nachweise

ORD-Eintrag
ord-dce0ea3a5ea74dc39414ff12a208c43e
Quelldatensatz
uspto-grants-2009_08
Patentnummer
US07572808B2

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