Sodium Carbonate → 6-(4-Carboxyphenyl)-8-methoxy-1,7-naphthyridine

HRID 369035

Reaktionsgleichung

Reaktionsgleichung von HRID 369035
FC(F)(F)S(O[C:7]1[CH:8]=[C:9]2[C:14](=[C:15]([O:17][CH3:18])[N:16]=1)[N:13]=[CH:12][CH:11]=[CH:10]2)(=O)=O.[C:21]([C:24]1[CH:29]=[CH:28][C:27](B(O)O)=[CH:26][CH:25]=1)([OH:23])=[O:22].C([O-])([O-])=O.[Na+].[Na+]>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.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C>[C:21]([C:24]1[CH:29]=[CH:28][C:27]([C:7]2[CH:8]=[C:9]3[C:14](=[C:15]([O:17][CH3:18])[N:16]=2)[N:13]=[CH:12][CH:11]=[CH:10]3)=[CH:26][CH:25]=1)([OH:23])=[O:22]

Komponenten

7

Edukt 3

HCID 10340Sodium CarbonateHCID 3121834-Carboxyphenylboronic AcidHCID 232846356-Trifluoromethylsulfonyloxy-8-methoxy-1,7-naphthyridine

Produkt 1

HCID 232846426-(4-Carboxyphenyl)-8-methoxy-1,7-naphthyridineAusbeute 80,8 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 80271Tri-o-tolylphosphineKatalysatorHCID 1542701,5-Diphenylpenta-1,4-dien-3-one;palladiumKatalysatorHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 6-trifluoromethylsulfonyloxy-8-methoxy-1,7-napthyridine (1.5 g, 4.86 mmol) in DMF (40 ml) is added 4-carboxy-phenylboronic acid (0.866 g, 5.34 mmol), bis(dibenzylidenacetone) palladium (112 mg, 0.167 mmol), tri-o-tolylphosphine (96 mg, 0.32 mmol) and aqueous Na2CO3 (14.6 ml, 2N,). The reaction mixture is stirred at 110° for 3 h. The hot solution is filtred through cellit and the solution evaporated to dryness. The crude product is dissolved in hot water (60 ml) and the water phase washed with ethyl acetate (3×50 ml). The product is precipitated from the water phase by carefully adding aqueous HCl (2N, 6 ml). The suspension is filtered and the crude product is stirred again in hot ethyl acetate (50 ml). The cold suspension is filtered to yield the title compound (1.10 g). M+280; Melting point >300°.

Aufarbeitung

  1. customthe solution evaporated to dryness
  2. dissolutionThe crude product is dissolved in hot water (60 ml)
  3. washthe water phase washed with ethyl acetate (3×50 ml)
  4. customThe product is precipitated from the water phase by carefully adding aqueous HCl (2N, 6 ml)
  5. filtrationThe suspension is filtered
  6. stirringthe crude product is stirred again in hot ethyl acetate (50 ml)
  7. filtrationThe cold suspension is filtered

Quellen und Nachweise

ORD-Eintrag
ord-449fc1ba55304cbb90163e63a52ba620
Quelldatensatz
uspto-grants-2000_10
Patentnummer
US06136821

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