Potassium Carbonate → HCID 67333397, compound

HRID 1804820Notes

Reaction equation

HRID 1804820 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([OH:11])=[CH:3][CH:2]=1.Br[CH2:13][C:14]1[CH:15]=[CH:16][C:17]([F:24])=[C:18]([CH:23]=1)[C:19]([O:21][CH3:22])=[O:20].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[F:24][C:17]1[CH:16]=[CH:15][C:14]([CH2:13][N:1]2[C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[C:4](=[O:11])[CH:3]=[CH:2]2)=[CH:23][C:18]=1[C:19]([O:21][CH3:22])=[O:20]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 22645461Methyl 5-(bromomethyl)-2-fluorobenzoateHCID 178516385quinolin-4-ol

Product 1

HCID 67333397HCID 67333397, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of quinolin-4-ol, methyl 5-(bromomethyl)-2-fluorobenzoate (prepared as described in US 2007/0021427 A1, 1 eq) and potassium carbonate (1.2 eq) in dry DMF (0.1 M solution) was stirred at 100° C. for 1 h. After solvent evaporation, the residue was dissolved in DCM and washed twice with H2O and once with brine. The organic phase was dried over Na2SO4 and concentrated to dryness under reduced pressure. The resulting crude was purified by flash-chromatography (EtOAc/PE 9:1) to give the title compound. The O-alkylated isomer is eluted before the title compound.

Workup

  1. customAfter solvent evaporation
  2. dissolutionthe residue was dissolved in DCM
  3. washwashed twice with H2O and once with brine
  4. dry with materialThe organic phase was dried over Na2SO4
  5. concentrationconcentrated to dryness under reduced pressure
  6. customThe resulting crude was purified by flash-chromatography (EtOAc/PE 9:1)

Sources & evidence

ORD record
ord-82638a5427384b5290c151f5c9ff24a0
Source dataset
uspto-grants-2013_01
Patent number
US08354413B2

Reaction notes

Loading…