3-Bromoaniline → 4-(3-Bromo-phenylamino)-6-fluoro-[1,7]naphthyridine-3-carbonitrile

HRID 276855Notes

Reaction equation

HRID 276855 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].[Br:15][C:16]1[CH:17]=[C:18]([CH:20]=[CH:21][CH:22]=1)[NH2:19]>C(O)C>[Br:15][C:16]1[CH:17]=[C:18]([NH:19][C:2]2[C:11]3[C:6](=[CH:7][N:8]=[C:9]([F:12])[CH:10]=3)[N:5]=[CH:4][C:3]=2[C:13]#[N:14])[CH:20]=[CH:21][CH:22]=1

Participants

4

Reactant 2

HCID 115623-BromoanilineHCID 185489604-Chloro-6-fluoro-1,7-naphthyridine-3-carbonitrile

Product 1

HCID 185489794-(3-Bromo-phenylamino)-6-fluoro-[1,7]naphthyridine-3-carbonitrileYield 87%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

To 1.9 g of 4-chloro-6-fluoro-[1.7]naphthyridine-3-carbonitrile in 30 mL of absolute ethanol was added 1.6 mL of 3-bromoaniline. After refluxing the reaction under an inert atmosphere for 8 hours, the reaction mixture was cooled to 0° C. and the product was filtered and washed with cold ethanol. Drying in vacuo yielded 2.7 g (87%) of 4-(3-bromo-phenylamino)-6-fluoro-[1.7]naphthyridine-3-carbonitrile as an off-white solid: melting point 185-195° C.; mass spectrum (m/e): M+H 343.0, 345.1.

Workup

  1. temperatureAfter refluxing
  2. customthe reaction under an inert atmosphere for 8 hours
  3. filtrationthe product was filtered
  4. washwashed with cold ethanol
  5. customDrying in vacuo

Sources & evidence

ORD record
ord-da8df5cd0c6e46409fd2ba0f86b44905
Source dataset
uspto-grants-2002_03
Patent number
US06355636B1

Reaction notes

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