4-(3-Bromo-phenylamino)-6-fluoro-[1,7]naphthyridine-3-carbonitrile → 4-(3-Bromo-phenylamino)-6-(2-dimethylamino-ethoxy)-[1,7]naphthyridine-3-carbonitrile
Reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[C:18]3[C:13](=[CH:14][N:15]=[C:16](F)[CH:17]=3)[N:12]=[CH:11][C:10]=2[C:20]#[N:21])[CH:5]=[CH:6][CH:7]=1.[CH3:22][N:23]([CH3:27])[CH2:24][CH2:25][O-:26].[Na+]>O1CCCC1.O>[Br:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[C:18]3[C:13](=[CH:14][N:15]=[C:16]([O:26][CH2:25][CH2:24][N:23]([CH3:27])[CH3:22])[CH:17]=3)[N:12]=[CH:11][C:10]=2[C:20]#[N:21])[CH:5]=[CH:6][CH:7]=1Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Procedure
To 100 mg of 4-(3-bromo-phenylamino)-6-fluoro-[1,7]naphthyridine-3-carbonitrile under an inert atmosphere was added 3 mL of 1 M sodium (2-dimethylamino-ethoxide) in tetrahydrofuran. After refluxing for 3 hours, the reaction was diluted with water and the product extracted five times with chloroform. The crude product was purified by flash chromatography with 1% triethyl amine and 10% methanol/chloroform followed by recrystallized from chloroform/ether to give 100 mg of 4-(3-bromo-phenylamino)-6-(2-dimethylamino-ethoxy)-[1,7]naphthyridine-3-carbonitrile as a yellow solid: melting point 138-139° C.; mass spectrum (m/e): M+H 411.9, 413.9.
Workup
- temperatureAfter refluxing for 3 hours
- extractionthe product extracted five times with chloroform
- customThe crude product was purified by flash chromatography with 1% triethyl amine and 10% methanol/chloroform
- customby recrystallized from chloroform/ether
Sources & evidence
- ORD record
- ord-c1d9330f24d042abaff061829df0c407
- Source dataset
- uspto-grants-2003_04
- Patent number
- US06548496B2
Reaction notes
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