1,2-Dimethoxyethane → HCID 66917053, compound

HRID 238335Notes

Reaction equation

HRID 238335 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([F:21])=[C:6]2[C:11]=1[NH:10][CH:9]=[C:8]([C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=1)[C:7]2=[O:20].[O:22]1[CH:26]=[CH:25][CH:24]=[C:23]1B(O)O.C(=O)([O-])[O-].[Na+].[Na+].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.ClCCl>[F:21][C:5]1[CH:4]=[CH:3][C:2]([C:23]2[O:22][CH:26]=[CH:25][CH:24]=2)=[C:11]2[C:6]=1[C:7](=[O:20])[C:8]([C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=1)=[CH:9][NH:10]2

Participants

7

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 10340Sodium CarbonateHCID 2734357Furan-2-boronic acidHCID 66917247HCID 66917247, compound

Product 1

HCID 66917053HCID 66917053, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 178418807HCID 178418807, compoundCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
180 °C

Procedure

8-bromo-5-fluoro-3-(4-methoxyphenyl)-1H-quinolin-4-one (150 mg, 0.43 mmol), 2-furan boronic acid (145 mg, 1.3 mmol), 1,1′-bis(diphenylphosphino)ferrocene dichloro palladium (II)-dichloromethane complex (PdCl2(DPPF)) (35 mg, 0.04 mmol) and a 2N sodium carbonate aqueous solution (1 ml) were added to 1,2-dimethoxyethane (3 ml), and the mixture was heated at 180° C. for 10 minutes (microwave reactor). After the reaction mixture was cooled to room temperature, dichloromethane was added, and then filtration with Celite was carried out. The filtrate was extracted with dichloromethane and washed with water. The organic layer was dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue was then purified by silica gel column chromatography (dichloromethane). The purified product was concentrated under reduced pressure, and the residue was recrystallized from n-hexane-ethyl acetate to thereby obtain 100 mg of powdery slightly orange 5-fluoro-8-furan-2-yl-3-(4-methoxyphenyl)-1H-quinolin-4-one (yield: 70%). Melting point 209-211° C.

Workup

  1. temperatureAfter the reaction mixture was cooled to room temperature
  2. filtrationfiltration with Celite
  3. extractionThe filtrate was extracted with dichloromethane
  4. washwashed with water
  5. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was then purified by silica gel column chromatography (dichloromethane)
  8. concentrationThe purified product was concentrated under reduced pressure
  9. customthe residue was recrystallized from n-hexane-ethyl acetate

Sources & evidence

ORD record
ord-f2d9fa112e664cea917b0a0064fbf439
Source dataset
uspto-grants-2014_02
Patent number
US08642619B2

Reaction notes

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