Sodium hydride → 8-bromo-7-fluoro-4,6-dimethylbenzo[c][2,7]naphthyridin-5(6H)-one

HRID 1398374Notes

Reaction equation

HRID 1398374 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:13]([C:14]([NH:16][CH3:17])=[O:15])=[C:12]([CH3:18])[N:11]=[CH:10][CH:9]=2)=[C:4](F)[C:3]=1[F:20].[H-].[Na+]>O1CCCC1.O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]2[C:8]3[C:13](=[C:12]([CH3:18])[N:11]=[CH:10][CH:9]=3)[C:14](=[O:15])[N:16]([CH3:17])[C:4]=2[C:3]=1[F:20]

Participants

5

Reactant 2

HCID 24758Sodium hydrideHCID 867103654-(4-bromo-2,3-difluorophenyl)-N,2-dimethylnicotinamide

Product 1

HCID 867103668-bromo-7-fluoro-4,6-dimethylbenzo[c][2,7]naphthyridin-5(6H)-oneYield 71%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-(4-bromo-2,3-difluorophenyl)-N,2-dimethylnicotinamide (600 mg, 1.76 mmol) in tetrahydrofuran (20 mL) at 0° C. was added NaH (176 mg, 4.40 mmol) and the reaction mixture was brought to room temperature gradually. The reaction mixture was stirred at room temperature for 15 h. The reaction mixture was diluted with water (50 mL) and extracted with ethyl acetate (100 mL). The organic layer was separated, dried over Na2SO4 and concentrated under reduced pressure to afford 8-bromo-7-fluoro-4,6-dimethylbenzo[c][2,7]naphthyridin-5(6H)-one (400 mg, 1.24 mmol, 71% yield) as yellow solid. LC/MS (ESI) m/e 322.8 [(M+2H)+, calcd for C14H12BrFN2O 322.9]; LC/MS retention time (method G): tR=2.21 min.

Workup

  1. customwas brought to room temperature
  2. extractionextracted with ethyl acetate (100 mL)
  3. customThe organic layer was separated
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-edaefa41c215487398b1a95fc299e68b
Source dataset
uspto-grants-2014_12
Patent number
US08901305B2

Reaction notes

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