Potassium Phosphate, Tribasic → 4-(7-(4-Chlorophenyl)-3-oxo-2-((6-(trifluoromethyl)pyridin-3-yl)methyl)-2,3-dihydro-[1,2,4]triazolo[4,3-a]pyridin-8-yl)benzaldehyde

HRID 2101307

Reaktionsgleichung

Reaktionsgleichung von HRID 2101307
Br[C:2]1[C:3]2[N:4]([C:15](=[O:29])[N:16]([CH2:18][C:19]3[CH:20]=[N:21][C:22]([C:25]([F:28])([F:27])[F:26])=[CH:23][CH:24]=3)[N:17]=2)[CH:5]=[CH:6][C:7]=1[C:8]1[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][CH:9]=1.[CH:30]([C:32]1[CH:37]=[CH:36][C:35](B(O)O)=[CH:34][CH:33]=1)=[O:31].C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>C(O)CCC.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[Cl:14][C:11]1[CH:10]=[CH:9][C:8]([C:7]2[CH:6]=[CH:5][N:4]3[C:15](=[O:29])[N:16]([CH2:18][C:19]4[CH:20]=[N:21][C:22]([C:25]([F:27])([F:26])[F:28])=[CH:23][CH:24]=4)[N:17]=[C:3]3[C:2]=2[C:35]2[CH:36]=[CH:37][C:32]([CH:30]=[O:31])=[CH:33][CH:34]=2)=[CH:13][CH:12]=1

Komponenten

7

Edukt 4

HCID 62657Potassium Phosphate, TribasicHCID 5910734-Formylphenylboronic AcidHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 577994658-bromo-7-(4-chlorophenyl)-2-((6-(trifluoromethyl)pyridin-3-yl)methyl)-[1,2,4]triazolo[4,3-a]pyridin-3(2H)-one

Produkt 1

HCID 577994634-(7-(4-Chlorophenyl)-3-oxo-2-((6-(trifluoromethyl)pyridin-3-yl)methyl)-2,3-dihydro-[1,2,4]triazolo[4,3-a]pyridin-8-yl)benzaldehyde

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 9811564Bis(dibenzylideneacetone)palladiumKatalysatorHCID 2631-ButanolLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

To a stirring solution of 8-bromo-7-(4-chlorophenyl)-2-((6-(trifluoromethyl)pyridin-3-yl)methyl)-[1,2,4]triazolo[4,3-a]pyridin-3(2H)-one (100 mg, 0.21 mmol) in n-butanol (1.6 mL) at room temperature under argon was added 4-formylphenylboronic acid (40.4 mg, 0.27 mmol), Pd2(dba)3 (7.6 mg, 0.008 mmol), dicyclohexyl(2′,6′-dimethoxybiphenyl-2-yl)phosphine (13.6 mg, 0.03 mmol) and K3PO4 (88.1 mg, 0.41 mmol). The resulting suspension was purged of oxygen by bubbling with argon for 15 min, sealed in a vial under argon, heated at 110° C. for 5 h, and then cooled to room temperature. The reaction mixture was diluted with EtOAc and washed once with water. The organic layer was dried (MgSO4), filtered, and concentrated under reduced pressure. The crude product was purified by automated silica gel chromatography (eluted with EtOAc/hexanes). Pooling of the desired fractions provided the title compound as a yellow solid, 38.8 mg, 36%. HPLC/MS: retention time=2.73 min, [M+H]+=509.

Aufarbeitung

  1. customThe resulting suspension was purged of oxygen
  2. customby bubbling with argon for 15 min
  3. customsealed in a vial under argon
  4. temperaturecooled to room temperature
  5. additionThe reaction mixture was diluted with EtOAc
  6. washwashed once with water
  7. dry with materialThe organic layer was dried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customThe crude product was purified by automated silica gel chromatography (eluted with EtOAc/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-8db678ef6d00497d87cf047f739f5a63
Quelldatensatz
uspto-grants-2009_08
Patentnummer
US07572808B2

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