Potassium Phosphate, Tribasic → N-[6-(3,6-Dihydro-2H-pyran-4-yl)-5-methylpyridin-3-yl]-5-methyl-1-[4-(trifluoromethyl)-phenyl]-1H-pyrazole-4-carboxamide

HRID 1748634Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1748634
[CH3:1][C:2]1[N:6]([C:7]2[CH:12]=[CH:11][C:10]([C:13]([F:16])([F:15])[F:14])=[CH:9][CH:8]=2)[N:5]=[CH:4][C:3]=1[C:17]([NH2:19])=[O:18].Br[C:21]1[CH:22]=[C:23]([CH3:33])[C:24]([C:27]2[CH2:28][CH2:29][O:30][CH2:31][CH:32]=2)=[N:25][CH:26]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>C(O)(C)(C)C.C(Cl)(Cl)Cl.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].C(P(C(C)(C)C)C1C(C)=C(C)C(C)=C(C)C=1C1C(C(C)C)=CC(C(C)C)=CC=1C(C)C)(C)(C)C>[O:30]1[CH2:31][CH:32]=[C:27]([C:24]2[N:25]=[CH:26][C:21]([NH:19][C:17]([C:3]3[CH:4]=[N:5][N:6]([C:7]4[CH:12]=[CH:11][C:10]([C:13]([F:16])([F:14])[F:15])=[CH:9][CH:8]=4)[C:2]=3[CH3:1])=[O:18])=[CH:22][C:23]=2[CH3:33])[CH2:28][CH2:29]1

Komponenten

8

Edukt 3

HCID 62657Potassium Phosphate, TribasicHCID 178227615-methyl-1-[4-(trifluoromethyl)phenyl]-1H-pyrazole-4-carboxamideHCID 866925085-Bromo-2-(3,6-dihydro-2H-pyran-4-yl)-3-methylpyridine

Produkt 1

HCID 86692571N-[6-(3,6-Dihydro-2H-pyran-4-yl)-5-methylpyridin-3-yl]-5-methyl-1-[4-(trifluoromethyl)-phenyl]-1H-pyrazole-4-carboxamideAusbeute 58 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 9811564Bis(dibenzylideneacetone)palladiumKatalysatorHCID 11953610Di-tert-butyl[3,4,5,6-tetramethyl-2',4',6'-tris(propan-2-yl)-[1,1'-biphenyl]-2-yl]phosphaneKatalysatorHCID 6212ChloroformLösungsmittelHCID 6386tert-ButanolLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

A suspension of 5-methyl-1-[4-(trifluoromethyl)phenyl]-1H-pyrazole-4-carboxamide (212 mg), 5-bromo-2-(3,6-dihydro-2H-pyran-4-yl)-3-methylpyridine (200 mg) described in Reference Example 135, 2-(di-tert-butylphosphino)-3,4,5,6-tetramethyl-2′,4′,6′-triisopropyl-1,1′-biphenyl (19 mg), tris(dibenzylideneacetone)dipalladium (0) (7.2 mg) and tripotassium phosphate (200 mg) in tert-butanol (3 ml) was stirred at 110° C. After the reaction, the reaction solution was left stand, diluted with chloroform and filtered through Celite. The organic layer was washed with water and saturated brine successively, dried over anhydrous sodium sulfate and concentrated. The resulting residue was purified with a silica gel column chromatography (chloroform/methanol), washed with hot ethanol and the resulting solid was filtered and dried at 60° C. in vacuo to give the titled compound (202 mg) as a white solid.

Aufarbeitung

  1. customAfter the reaction
  2. waitthe reaction solution was left stand
  3. filtrationfiltered through Celite
  4. washThe organic layer was washed with water and saturated brine successively
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated
  7. customThe resulting residue was purified with a silica gel column chromatography (chloroform/methanol)
  8. washwashed with hot ethanol
  9. filtrationthe resulting solid was filtered
  10. customdried at 60° C. in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-0436c03475aa45f292880c1dbd83ddd1
Quelldatensatz
uspto-grants-2015_10
Patentnummer
US09150555B2

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