(4-Aminophenoxy)benzene → 6-Fluoro-4-(4-phenoxyanilino)-1,7-naphthyridine-3-carbonitrile

HRID 276863

Reaction equation

HRID 276863 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][N:8]=[C:9]([F:12])[CH:10]=2)[N:5]=[CH:4][C:3]=1[C:13]#[N:14].[O:15]([C:22]1[CH:28]=[CH:27][C:25]([NH2:26])=[CH:24][CH:23]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(=O)(O)[O-].[Na+]>CO.[Cl-].[Na+].O>[F:12][C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][N:8]=1)[N:5]=[CH:4][C:3]([C:13]#[N:14])=[C:2]2[NH:26][C:25]1[CH:24]=[CH:23][C:22]([O:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:28][CH:27]=1

Participants

6

Reactant 3

HCID 8764(4-Aminophenoxy)benzeneHCID 516892Sodium BicarbonateHCID 185489604-Chloro-6-fluoro-1,7-naphthyridine-3-carbonitrile

Product 1

HCID 185489566-Fluoro-4-(4-phenoxyanilino)-1,7-naphthyridine-3-carbonitrileYield 69%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To 2.0 g of 4-chloro-6-fluoro-[1.7]naphthyridine-3-carbonitrile in 50 mL of methanol was added 2.2 g of 4-phenoxyaniline. After stirring the reaction under an inert atmosphere for 18 hr, the reaction mixture was poured into a mixture of brine and saturated aqueous sodium bicarbonate and the resultant crystals filtered and washed with water. The product was then recrystallized from chloroformhexanes. Drying in vacuo yielded 2.35 g (69%) of 6-fluoro-4-(4-phenoxy-phenylamino)-[1.7]naphthyridine-3-carbonitrile as yellow needles: melting point 211-213° C.; mass spectrum (m/e): M+H 356.9.

Workup

  1. customthe reaction under an inert atmosphere for 18 hr
  2. filtrationthe resultant crystals filtered
  3. washwashed with water
  4. customThe product was then recrystallized from chloroformhexanes
  5. customDrying in vacuo

Sources & evidence

ORD record
ord-d0aa85005d3e41988f68ffd694a1f31c
Source dataset
uspto-grants-2002_03
Patent number
US06355636B1

Linked notes

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