Benzyl Bromide → HCID 86723584, compound

HRID 918912Notes

Reaction equation

HRID 918912 reaction equation
[Br:1][C:2]1[C:11]2[N:10]=[CH:9][CH:8]=[CH:7][C:6]=2[C:5](=[O:12])[NH:4][CH:3]=1.[H-].[Na+].[CH2:15](Br)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[NH4+].[Cl-]>CN(C=O)C.O>[CH2:15]([N:4]1[CH:3]=[C:2]([Br:1])[C:11]2[N:10]=[CH:9][CH:8]=[CH:7][C:6]=2[C:5]1=[O:12])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

7

Reactant 4

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 218622158-Bromo-1,6-naphthyridin-5(6H)-one

Product 1

HCID 86723584HCID 86723584, compoundYield 86%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 8-bromo-1,6-naphthyridin-5(6H)-one (0.225 g, 1.0 mmol) in anhydrous DMF (6 mL) was added sodium hydride (60% dispersion in mineral oil, 0.052 g, 1.3 mmol) at 0° C. The resulting mixture was stirred at 0° C. for 45 min and then benzyl bromide (0.205 g, 1.2 mmol) was added slowly. The reaction mixture was stirred at 0° C. for 2 h, then allowed to warm to rt and stirred for 17 h. After that time, saturated NH4Cl solution (5 mL) and water (5 mL) were added and the mixture was extracted with ethyl acetate (2×25 mL). The organic phase was washed with brine, dried over Na2SO4, filtered and concentrated under reduced pressure. The product was purified by flash column chromatography (silica gel, 99:1 dichloromethane/methanol to 97:3 dichloromethane/methanol) to give 6-benzyl-8-bromo-1,6-naphthyridin-5(6H)-one (0.270 g, 86%) as an off-white solid: 1H NMR (400 MHz, CDCl3) δ 9.04 (dd, J=4.5, 1.8 Hz, 1H), 8.71-8.77 (m, 1H), 7.65 (s, 1H), 7.50 (dd, J=8.0, 4.5 Hz, 1H), 7.30-7.41 (m, 5H), 5.22 (s, 2H); ESI MS m/z 315 [M+H]+ and 317 [M+H]+.

Workup

  1. stirringThe reaction mixture was stirred at 0° C. for 2 h
  2. temperatureto warm to rt
  3. stirringstirred for 17 h
  4. extractionthe mixture was extracted with ethyl acetate (2×25 mL)
  5. washThe organic phase was washed with brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe product was purified by flash column chromatography (silica gel, 99:1 dichloromethane/methanol to 97:3 dichloromethane/methanol)

Sources & evidence

ORD record
ord-d027577f9f2f412ea5526dad0f6a9461
Source dataset
uspto-grants-2016_03
Patent number
US09271978B2

Reaction notes

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