Benzyl Bromide → HCID 86723590, compound

HRID 918918Notes

Reaction equation

HRID 918918 reaction equation
[CH2:1](Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[I:9][C:10]1[C:19]2[C:14](=[CH:15][CH:16]=[N:17][CH:18]=2)[C:13](=[O:20])[NH:12][CH:11]=1.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C>[CH2:1]([N:12]1[CH:11]=[C:10]([I:9])[C:19]2[C:14](=[CH:15][CH:16]=[N:17][CH:18]=2)[C:13]1=[O:20])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 10796Cesium carbonateHCID 66631598HCID 66631598, compound

Product 1

HCID 86723590HCID 86723590, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

Benzyl bromide (0.057 g, 0.34 mmol) was added to a mixture of 4-iodo-2,6-naphthyridin-1(2H)-one trifluororoacetate (0.100 g, 0.26 mmol) and Cs2CO3 (0.253 g, 0.78 mmol) in anhydrous DMF (10 mL) cooled to 0° C. The reaction was stirred at 0° C. for 30 min, then allowed to warm to rt and stirred for 17 h. After that time the reaction was concentrated under reduced pressure, diluted with water (10 mL), and 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 2-benzyl-4-iodo-2,6-naphthyridin-1(2H)-one (0.070 g, 74%) as an off-white solid: 1H NMR (400 MHz, CDCl3) δ 9.04 (s, 1H), 8.78 (d, J=5.3 Hz, 1H), 8.14 (d, J=5.3 Hz, 1H), 7.57 (s, 1H), 7.31-7.40 (m, 5H), 5.20 (s, 2H); ESI MS m/z 363 [M+H]+.

Workup

  1. temperatureto warm to rt
  2. stirringstirred for 17 h
  3. concentrationAfter that time the reaction was concentrated under reduced pressure
  4. additiondiluted with water (10 mL)
  5. extractionextracted with ethyl acetate (2×25 mL)
  6. washThe organic phase was washed with brine
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customThe product was purified by flash column chromatography (silica gel, 99:1 dichloromethane/methanol to 97:3 dichloromethane/methanol)

Sources & evidence

ORD record
ord-410381423e24477290972cb996233581
Source dataset
uspto-grants-2016_03
Patent number
US09271978B2

Reaction notes

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