Water → HCID 66917345, compound

HRID 1477138Notes

Reaction equation

HRID 1477138 reaction equation
[F:1][C:2]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][CH2:14][CH3:15])=[C:8]2[C:3]=1[C:4](=[O:17])[C:5](I)=[CH:6][NH:7]2.[N:18]1[CH:23]=[CH:22][CH:21]=[C:20](B(O)O)[CH:19]=1.C(=O)([O-])[O-].[Na+].[Na+].O>COCCOC.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].ClCCl>[F:1][C:2]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][CH2:14][CH3:15])=[C:8]2[C:3]=1[C:4](=[O:17])[C:5]([C:20]1[CH:19]=[N:18][CH:23]=[CH:22][CH:21]=1)=[CH:6][NH:7]2

Participants

7

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 27343783-Pyridinylboronic acidHCID 66917332HCID 66917332, compound

Product 1

HCID 66917345HCID 66917345, compoundYield 36%

Reagents, catalysts & solvents 2

HCID 178418807HCID 178418807, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
90 °C

Procedure

5-Fluoro-3-iodo-8-propoxy-1H-quinolin-4-one (600 mg, 1.73 mmol) was suspended in 1,2-dimethoxyethane (12 ml). 3-pyridine boronic acid (752 mg), 1,1′-bis(diphenylphosphino)ferrocene dichloro palladium(II)-dichloromethane complex (PdCl2(DPPF)) (76 mg, 0.093 mmol), and 2N sodium carbonate aqueous solution (2.54 ml) were added to the resulting suspension in that order. The mixture was stirred at 90° C. for 2 hours under a nitrogen atmosphere. After the reaction mixture was cooled to room temperature, water was added, and the resulting mixture was extracted with ethyl acetate. The organic layer was concentrated under reduced pressure, and the residue was then purified by silica gel column chromatography (dichloromethane:methanol=15:1). The purified product was concentrated under reduced pressure, and then recrystallized from ethanol to thereby obtain 185 mg of powdery pale brown 5-fluoro-8-propoxy-3-pyridin-3-yl-1H-quinolin-4-one (yield: 36%).

Workup

  1. temperatureAfter the reaction mixture was cooled to room temperature
  2. extractionthe resulting mixture was extracted with ethyl acetate
  3. concentrationThe organic layer was concentrated under reduced pressure
  4. customthe residue was then purified by silica gel column chromatography (dichloromethane:methanol=15:1)
  5. concentrationThe purified product was concentrated under reduced pressure
  6. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-4ff54e9a7bca49b8a62d22bbd9aad738
Source dataset
uspto-grants-2016_08
Patent number
US09403773B2

Reaction notes

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