Methanol → 2-(4-Bromo-2-fluorophenylamino)-6-oxo-1,6-dihydropyridine-3-carboxylic acid

HRID 422796Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 422796
C[O:2][C:3](=[O:21])[C:4]1[CH:9]=[CH:8][C:7]([O:10]C)=[N:6][C:5]=1[NH:12][C:13]1[CH:18]=[CH:17][C:16]([Br:19])=[CH:15][C:14]=1[F:20].COC(=O)C1C=CC(Cl)=NC=1NC1C=CC(Br)=CC=1F.C[O-].[Na+].CO>C(O)(=O)C>[Br:19][C:16]1[CH:17]=[CH:18][C:13]([NH:12][C:5]2[NH:6][C:7](=[O:10])[CH:8]=[CH:9][C:4]=2[C:3]([OH:21])=[O:2])=[C:14]([F:20])[CH:15]=1

Komponenten

6

Edukt 4

HCID 887MethanolHCID 10942334Sodium Methoxide2×HCID 666734732-(4-Bromo-2-fluorophenylamino)-6-methoxy-nicotinic acid methyl esterHCID 866723242-(4-Bromo-2-fluorophenylamino)-6-chloro-nicotinic acid methyl ester

Produkt 1

HCID 576368232-(4-Bromo-2-fluorophenylamino)-6-oxo-1,6-dihydropyridine-3-carboxylic acidAusbeute 88 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Reaktionsbedingungen

Temperatur
62.5 °C

Versuchsvorschrift

Preparation of 2-(4-bromo-2-fluorophenylamino)-6-methoxynicotinic acid methyl ester: To a mixture of 2-(4-bromo-2-fluorophenylamino)-6-chloronicotinic acid methyl ester (2.00 g, 5.56 mmol) and sodium methoxide (0.791 g, 13.9 mmol) was added MeOH (50 mL) to give a slurry that was stirred at 60-65° C. for 16 hours under N2. Additional sodium methoxide (0.791 g, 13.9 mmol) was added and the reaction mixture was allowed to stir another 3 days at 60-65° C. The reaction mixture was cooled to room temperature and glacial acetic acid was added dropwise until the pH was 7. The resulting suspension was filtered and washed with H2O to yield a pink solid that was collected and dried under vacuum to yield 1.74 g (88%) pure desired product.

Aufarbeitung

  1. customto give a slurry that
  2. stirringto stir another 3 days at 60-65° C
  3. temperatureThe reaction mixture was cooled to room temperature
  4. filtrationThe resulting suspension was filtered
  5. washwashed with H2O
  6. customto yield a pink solid
  7. customthat was collected
  8. customdried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-0e46226e195b41f7b32a8a3b583352e5
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08101639B2

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