Iodine → HCID 59634716, compound

HRID 405993Notes

Reaction equation

HRID 405993 reaction equation
[CH2:1]([C:3]1[NH:4][C:5]2[C:10]([C:11](=[O:13])[CH:12]=1)=[CH:9][C:8]([F:14])=[CH:7][CH:6]=2)[CH3:2].[I:15]I.C([O-])([O-])=O.[Na+].[Na+].[O-]S([O-])(=S)=O.[Na+].[Na+]>C1COCC1>[CH2:1]([C:3]1[NH:4][C:5]2[C:10]([C:11](=[O:13])[C:12]=1[I:15])=[CH:9][C:8]([F:14])=[CH:7][CH:6]=2)[CH3:2]

Participants

6

Reactant 4

HCID 807IodineHCID 10340Sodium CarbonateHCID 24477Sodium ThiosulfateHCID 15114584135077-31-5

Product 1

HCID 59634716HCID 59634716, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A stirred mixture of 2-ethyl-6-fluoroquinolin-4(1H)-one (4.00 g, 21 mmol), I2 (10.62 g, 2.0 eq) and Na2CO3 (3.33 g, 1.5 eq) in THF (100 mL) was stirred at rt overnight. To the reaction mixture was added Na2S2O3 solution, after 2 min the resulted mixture was filtered, washed with water and dried in the air to give a white solid as 2-ethyl-6-fluoro-3-iodoquinolin-4(1H)-one. Mass Spectrum (ESI) m/e=318 (M+1). A mixture of 2-ethyl-6-fluoro-3-iodoquinolin-4(1H)-one (400 mg, 1.3 mmol), 3,5-difluorophenylboronic acid (398 mg, 2.0 eq), Na2CO3 (401 mg, 3.0 eq) and tetrakis(triphenylphosphine)palladium(0) (73 mg, 0.05 eq) in acetonitrile/water (15 mL/5 mL) was purged with N2 and heated to reflux. After overnight, the reaction mixture was cooled at rt, partitioned between water and EtOAc. The layers were separated and the aq layer was extracted with EtOAc (10 mL×2). The combined organic layers were washed with water (10 mL×2), brine (10 mL), dried over Na2SO4, filtered, and concd under reduced pressure. The residue was purified by combiflash on silica gel (EtOAc/DCM, 1:2) to give 3-(3,5-difluorophenyl)-2-ethyl-6-fluoroquinolin-4(1H)-one as a white solid. Mass Spectrum (ESI) m/e=304 (M+1).

Workup

  1. filtrationafter 2 min the resulted mixture was filtered
  2. washwashed with water
  3. customdried in the air

Sources & evidence

ORD record
ord-9d73c4ebdc44454ab887fa7977b0d51c
Source dataset
uspto-grants-2014_06
Patent number
US08754089B2

Reaction notes

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