Water → HCID 19709967, compound

HRID 725889Notes

Reaction equation

HRID 725889 reaction equation
Cl[C:2]1[CH:11]=[C:10]([CH2:12][CH2:13][NH:14][C:15](=[O:20])[C:16]([F:19])([F:18])[F:17])[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([O:21][CH3:22])[CH:8]=2)[N:3]=1.[C:23]1(OB(O)O)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C(=O)([O-])[O-].[Na+].[Na+].O>C1C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:22][O:21][C:7]1[CH:8]=[C:9]2[C:4](=[CH:5][CH:6]=1)[N:3]=[C:2]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[CH:11]=[C:10]2[CH2:12][CH2:13][NH:14][C:15](=[O:20])[C:16]([F:19])([F:18])[F:17]

Participants

7

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 78412Phenyl dihydrogen orthoborateHCID 19709972HCID 19709972, compound

Product 1

HCID 19709967HCID 19709967, compoundYield 91,713%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 241BenzeneSolvent

Procedure

A solution of N-[2-(2-chloro-6-methoxyquinolin-4-yl)ethyl]-2,2,2-trifluoroacetamide (0.5 g, 1.5 mmol), tetrakis(triphenylphosphine)palladium (58 mg, 0.05 mmol) and phenylboric acid (0.2 g, 1.65 mmol) in benzene (4.2 ml) was mixed with an aqueous solution (1.9 ml) of sodium carbonate (2 mol). This reaction mixture was heated under reflux in an atmosphere of argon for 64 hours. The reaction mixture was poured into water, and the organic layer was extracted with ethyl acetate. The extract was washed with saturated brine and water and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The resulting residue was purified by column chromatography on silica gel (ethyl acetate:hexane=4:6) to obtain the title compound (515 g, 91%).

Workup

  1. temperatureThis reaction mixture was heated
  2. temperatureunder reflux in an atmosphere of argon for 64 hours
  3. extractionthe organic layer was extracted with ethyl acetate
  4. washThe extract was washed with saturated brine and water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. customThe resulting residue was purified by column chromatography on silica gel (ethyl acetate:hexane=4:6)

Sources & evidence

ORD record
ord-ffffbcff0092449bb38db7b667475813
Source dataset
uspto-grants-1998_01
Patent number
US05708005

Reaction notes

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