Potassium Carbonate → 6-(4-Carboxyphenyl)-8-(3-cyanophenyl)-1,7-naphthyridine

HRID 369033

Reaktionsgleichung

Reaktionsgleichung von HRID 369033
FC(F)(F)S(O[C:7]1[CH:8]=[C:9]2[C:14](=[C:15]([C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([C:23]#[N:24])[CH:18]=3)[N:16]=1)[N:13]=[CH:12][CH:11]=[CH:10]2)(=O)=O.[C:27]([C:30]1[CH:35]=[CH:34][C:33](B(O)O)=[CH:32][CH:31]=1)([OH:29])=[O:28].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.[Pd].C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1>[C:27]([C:30]1[CH:35]=[CH:34][C:33]([C:7]2[CH:8]=[C:9]3[C:14](=[C:15]([C:17]4[CH:22]=[CH:21][CH:20]=[C:19]([C:23]#[N:24])[CH:18]=4)[N:16]=2)[N:13]=[CH:12][CH:11]=[CH:10]3)=[CH:32][CH:31]=1)([OH:29])=[O:28]

Komponenten

7

Edukt 4

HCID 11430Potassium CarbonateHCID 11776TriphenylphosphineHCID 3121834-Carboxyphenylboronic AcidHCID 10571743Trifluoro-methanesulfonic acid 8-(3-cyano-phenyl)-[1,7]naphthyridin-6-yl ester

Produkt 1

HCID 99283906-(4-Carboxyphenyl)-8-(3-cyanophenyl)-1,7-naphthyridineAusbeute 56,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1542701,5-Diphenylpenta-1,4-dien-3-one;palladiumKatalysatorHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 6-trifluoromethylsulfonyloxy-8-(3-cyanophenyl)-1,7-napthyridine (2.15 g, 5.67 mmol) in DMF (21.5 ml) is added 4-carboxy-phenylboronic acid (1.13 g, 6.81 mmol), bis(dibenzylidenacetone) palladium (131 mg, 0.23 mmol), triphenylphosphine (95 mg, 0.36 mmol) and aqueous K2CO3 (2N, 17 ml). The reaction mixture is stirred at 80° for 2.5 h. The hot solution is filtered through cellit and the crude product is precipitated by carefully adding water (10 ml) and aqueous HCl (2N, 8 ml). The suspension is filtered and the crude product is stirred in hot THF (30 ml). The cold suspension is filtered again to yield the title compound (1.12 g). M+H=352. Melting point >300°. Retention time HPLC=7.58 min (column: LiChroCart 125-4, Supersphere 60 RP-select B, 400; eluent: acetonitrile-water (0.1% TFA)=45:55; 1 ml/min; detection at 254 nm).

Aufarbeitung

  1. filtrationThe hot solution is filtered through cellit
  2. customthe crude product is precipitated by carefully adding water (10 ml) and aqueous HCl (2N, 8 ml)
  3. filtrationThe suspension is filtered
  4. stirringthe crude product is stirred in hot THF (30 ml)
  5. filtrationThe cold suspension is filtered again

Quellen und Nachweise

ORD-Eintrag
ord-3fd7c358944347ac925b015aa64e3bf0
Quelldatensatz
uspto-grants-2000_10
Patentnummer
US06136821

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