Dimethylformamide → HCID 66917315, compound

HRID 238325Notes

Reaction equation

HRID 238325 reaction equation
C(=O)([O-])[O-].[K+].[K+].CN(C=O)C.[CH:12]1([CH2:15][O:16][C:17]2[CH:18]=[CH:19][C:20]([F:29])=[C:21]3[C:26]=2[NH:25][CH:24]=[C:23]([I:27])[C:22]3=[O:28])[CH2:14][CH2:13]1.[CH2:30](I)[CH3:31]>O>[CH:12]1([CH2:15][O:16][C:17]2[CH:18]=[CH:19][C:20]([F:29])=[C:21]3[C:26]=2[N:25]([CH2:30][CH3:31])[CH:24]=[C:23]([I:27])[C:22]3=[O:28])[CH2:13][CH2:14]1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 66917216HCID 66917216, compound

Product 1

HCID 66917315HCID 66917315, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Potassium carbonate (450 mg, 3.26 mmol) was added to a DMF solution (5 ml) of 8-cyclopropylmethoxy-5-fluoro-3-iodo-1H-quinolin-4-one (910 mg, 2.53 mmol). The mixture was stirred for 15 minutes at room temperature. Ethyl iodide (0.31 ml, 3.87 mmol) was added thereto, and the resulting mixture was stirred at 60° C. for 2 hours. 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:ethyl acetate=40:1→15:1). The purified product was concentrated to dryness under reduced pressure to thereby obtain 750 mg of powdery pale dark brown 8-cyclopropylmethoxy-1-ethyl-5-fluoro-3-iodo-1H-quinolin-4-one (yield: 77%).

Workup

  1. stirringthe resulting mixture was stirred at 60° C. for 2 hours
  2. temperatureAfter the reaction mixture was cooled to room temperature
  3. extractionthe resulting mixture was extracted with ethyl acetate
  4. concentrationThe organic layer was concentrated under reduced pressure
  5. customthe residue was then purified by silica gel column chromatography (dichloromethane:ethyl acetate=40:1→15:1)
  6. concentrationThe purified product was concentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-224b59e31f6b458281160ad408491c0e
Source dataset
uspto-grants-2014_02
Patent number
US08642619B2

Reaction notes

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