Potassium Carbonate → HCID 22050892, compound

HRID 1866980Notes

Reaction equation

HRID 1866980 reaction equation
[Br:1][C:2]1[C:3](=[O:17])[N:4]([CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([F:16])[CH:11]=2)[CH:5]=[CH:6][C:7]=1[OH:8].C(=O)([O-])[O-].[K+].[K+].Br[CH:25]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[CH3:26]>CN(C=O)C>[Br:1][C:2]1[C:3](=[O:17])[N:4]([CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([F:16])[CH:11]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH:25]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[CH3:26]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 11454(1-Bromoethyl)benzeneHCID 54724177HCID 54724177, compound

Product 1

HCID 22050892HCID 22050892, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 3-bromo-1-(3-fluorobenzyl)-4-hydroxypyridin-2(1H)-one (0.2 g, 0.72 mmol), potassium carbonate (0.1 g, 0.72 mmol) and (1-bromoethyl)benzene (0.19 g, 1 mmol) in DMF (3.0 mL) was stirred at room temperature for 16 h. DMF was distilled in vacuo, and the residue was purified by flash chromatography (EtOAc in hexane (1:3 v/v) to give pale yellow syrup. This material was further purified by reverse-phase HPLC using 10-90% acetonitrile/water gradient (30 min), at flow rate of 100 mL/min. The appropriate fractions were combined, concentrated to a small volume (20 mL), added EtOAc (25 mL) and washed successively with satd. sod. bicarbonate, water, and dried (Na2SO4). EtOAc was removed under reduced pressure and residue was dried in vacuo to afford the title compound (0.15 g, 52%) as an amorphous substance: 1H NMR (CD3OD/400 MHz) δ 7.56 (d, 1H, J=7.6 Hz), 7.4-7.2 (m, 5H), 7.0 (m, 3H), 6.28 (d, 1H, J=7.6 Hz), 5.65 (m, 1H), 5.19 (d×d, 2H, J=14.8 Hz), and 1.64 (d, 3H, J=6.4 Hz), ES-HRMS m/z 402.0492 (M+H C20H18NO2Br, requires 402.0499).

Workup

  1. distillationDMF was distilled in vacuo
  2. customthe residue was purified by flash chromatography (EtOAc in hexane (1:3 v/v)
  3. customto give pale yellow syrup
  4. customThis material was further purified by reverse-phase
  5. custom10-90% acetonitrile/water gradient (30 min)
  6. concentrationconcentrated to a small volume (20 mL)
  7. additionadded EtOAc (25 mL)
  8. washwashed successively with satd
  9. dry with materialbicarbonate, water, and dried (Na2SO4)
  10. customEtOAc was removed under reduced pressure and residue
  11. customwas dried in vacuo

Sources & evidence

ORD record
ord-b6287aae5a454fb8b4e2cd40771553b0
Source dataset
uspto-grants-2009_12
Patent number
US07629363B2

Reaction notes

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