Sodium hydride → HCID 86710330, compound

HRID 1398326Notes

Reaction equation

HRID 1398326 reaction equation
[H-].[Na+].[Cl:3][C:4]1[C:9]([F:10])=[CH:8][C:7]([C:11]2[C:16]([C:17]([NH:19][CH3:20])=[O:18])=[CH:15][N:14]=[CH:13][CH:12]=2)=[C:6](F)[CH:5]=1>C1COCC1>[Cl:3][C:4]1[C:9]([F:10])=[CH:8][C:7]2[C:11]3[C:16](=[CH:15][N:14]=[CH:13][CH:12]=3)[C:17](=[O:18])[N:19]([CH3:20])[C:6]=2[CH:5]=1

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 86710329HCID 86710329, compound

Product 1

HCID 86710330HCID 86710330, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of sodium hydride (56.6 mg, 1.42 mmol) in THF (5 mL) at 0° C. was slowly added 4-(4-chloro-2,5-difluorophenyl)-N-methylnicotinamide (100 mg, 0.354 mmol) in THF (5 mL). The resultant mixture was stirred at room temperature for 1 h. The reaction was then quenched by addition of cold water (1 mL) and extracted with ethyl acetate (2×2 mL). The combined organic extracts were dried with sodium sulfate and concentrated under reduced pressure. The residue was purified by column chromatography (1:1 ethyl acetate in petroleum ether) to afford 8-chloro-9-fluoro-6-methylbenzo[c][2,7]naphthyridin-5(6H)-one (82 mg, 0.297 mmol, 84% yield) as white solid. LC/MS (ESI) m/e 262.5 [(M+H)+, calcd for C13H9ClFN2O 263.0]; LC/MS retention time (method D): tR=1.79 min; HPLC retention time (method A): tR=7.35 min; HPLC retention time (method B): tR=7.07 min.

Workup

  1. customThe reaction was then quenched by addition of cold water (1 mL)
  2. extractionextracted with ethyl acetate (2×2 mL)
  3. dry with materialThe combined organic extracts were dried with sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by column chromatography (1:1 ethyl acetate in petroleum ether)

Sources & evidence

ORD record
ord-ab2b9e4b87d147cd94f9139778cabab6
Source dataset
uspto-grants-2014_12
Patent number
US08901305B2

Reaction notes

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