Toluene → HCID 66917306, compound

HRID 1477137Notes

Reaction equation

HRID 1477137 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.C1(C)C=CC=CC=1.[O:25]1[CH:29]=[CH:28][C:27](B(O)O)=[CH:26]1.C(=O)([O-])[O-].[Na+].[Na+]>O.CO>[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:27]1[CH:28]=[CH:29][O:25][CH:26]=1)=[CH:6][NH:7]2

Participants

7

Reactant 4

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 2734358Furan-3-boronic acidHCID 66917332HCID 66917332, compound

Product 1

HCID 66917306HCID 66917306, compoundYield 58%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
110 °C

Procedure

5-Fluoro-3-iodo-8-propoxy-1H-quinolin-4-one (780 mg, 2.24 mmol) was suspended in a mixed solvent of toluene (10 ml) and methanol (1.6 ml), and furan-3-boronic acid (752 mg), tetrakis triphenylphosphine palladium (130 mg, 0.11 mmol), and a 2N sodium carbonate aqueous solution (2.25 ml) were added thereto in that order. The mixture was stirred under a nitrogen atmosphere at 110° C. for 20 hours. After the reaction mixture was cooled to room temperature, water was added, and the resulting mixture was extracted with dichloromethane. The organic layer was concentrated under reduced pressure, the residue was then purified by silica gel column chromatography (dichloromethane:methanol=60:1→50:1). The purified product was concentrated under reduced pressure and was recrystallized from ethanol to thereby obtain 180 mg of powdery pale yellow 5-fluoro-3-furan-3-yl-8-propoxy-1H-quinolin-4-one (yield: 58%).

Workup

  1. temperatureAfter the reaction mixture was cooled to room temperature
  2. extractionthe resulting mixture was extracted with dichloromethane
  3. concentrationThe organic layer was concentrated under reduced pressure
  4. customthe residue was then purified by silica gel column chromatography (dichloromethane:methanol=60:1→50:1)
  5. concentrationThe purified product was concentrated under reduced pressure
  6. customwas recrystallized from ethanol

Sources & evidence

ORD record
ord-3a189829951640f3ad46da410ccc278a
Source dataset
uspto-grants-2016_08
Patent number
US09403773B2

Reaction notes

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