Ethyl Acetate → HCID 178506293, compound

HRID 921520Notes

Reaction equation

HRID 921520 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[NH:8][N:9]=[C:10]([C:11]([F:14])([F:13])[F:12])[C:3]=12.[N:15]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH:18]=[C:17](B(O)O)[CH:16]=1.C(=O)([O-])[O-].[Na+].[Na+].C(OCC)(=O)C>O1CCOCC1.O>[F:12][C:11]([F:14])([F:13])[C:10]1[C:3]2[C:4](=[N:5][CH:6]=[CH:7][C:2]=2[C:17]2[CH:16]=[N:15][C:24]3[C:19]([CH:18]=2)=[CH:20][CH:21]=[CH:22][CH:23]=3)[NH:8][N:9]=1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 10340Sodium CarbonateHCID 2734663Quinoline-3-boronic acidHCID 178506294HCID 178506294, compound

Product 1

HCID 178506293HCID 178506293, compoundYield 33.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

A [1,1-bis-(diphenylphosphino)-ferrocene]dichloropalladium(II) dichloromethane complex (0.74 g) was added to a solution of compound (1c) (2.0 g), quinoline-3-boronic acid (2.5 g), and an aqueous sodium carbonate solution (1 M, 18 mL) in 1,4-dioxane (45 mL) under a nitrogen atmosphere, followed by stirring at 100° C. for 3 hr. The reaction solution was distributed between ethyl acetate and water, and the organic layer was washed with saturated saline and then dried over anhydrous sodium sulfate. After distillation of the solvent, the residue was purified by neutral silica gel column chromatography (chloroform/methanol) to obtain compound (1d) (0.94 g, 33%) as a white solid.

Workup

  1. washthe organic layer was washed with saturated saline
  2. dry with materialdried over anhydrous sodium sulfate
  3. distillationAfter distillation of the solvent
  4. customthe residue was purified by neutral silica gel column chromatography (chloroform/methanol)

Sources & evidence

ORD record
ord-24026c2aec0143aba9b1665123b73448
Source dataset
uspto-grants-2016_03
Patent number
US09273045B2

Reaction notes

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