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Potassium Carbonate → Ethyl 6-iodo-1-(1-methoxy-3-methylbutan-2-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylate

HRID 2061863
Notes
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Reaction equation

HRID 2061863 reaction equation
CN(C)/[CH:3]=[C:4](/[C:10](=[O:19])[C:11]1[CH:16]=[C:15]([I:17])[CH:14]=[CH:13][C:12]=1F)\[C:5]([O:7][CH2:8][CH3:9])=[O:6].Cl.[CH3:22][O:23][CH2:24][CH:25]([NH2:29])[CH:26]([CH3:28])[CH3:27].C(=O)([O-])[O-].[K+].[K+]>C1COCC1>[I:17][C:15]1[CH:16]=[C:11]2[C:12](=[CH:13][CH:14]=1)[N:29]([CH:25]([CH:26]([CH3:28])[CH3:27])[CH2:24][O:23][CH3:22])[CH:3]=[C:4]([C:5]([O:7][CH2:8][CH3:9])=[O:6])[C:10]2=[O:19]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 196933671-Methoxy-3-methyl-2-butanamine hydrochlorideHCID 70809441(Z)-ethyl 3-(dimethylamino)-2-(2-fluoro-5-iodobenzoyl)acrylate2×

Product 1

HCID 67029012Ethyl 6-iodo-1-(1-methoxy-3-methylbutan-2-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylateYield 60%

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent

Conditions

Temperature
60 °C

Procedure

To a solution of ethyl 3-(dimethylamino)-2-(2-fluoro-5-iodobenzoyl)acrylate (Intermediate 24, 1 g, 2.56 mmol) dissolved in THF (10 mL) was added 1-methoxy-3-methylbutan-2-amine hydrochloride (366 mg, 2.38 mmol) followed by potassium carbonate. The reaction mixture was stirred at 60° C. for 2 d. The reaction mixture was concentrated under reduced pressure and the residue was resuspended in DMF (10 mL). Potassium carbonate was added (978 mg, 7.08 mmol), and the reaction mixture was stirred at 70° C. for 2 h. The reaction mixture was cooled down to room temperature and quenched with 1 N HCl. The reaction mixture was partitioned between water (20 mL) and ethyl acetate (20 mL). The aqueous layer was extracted with ethyl acetate, and the organics were dried and concentrated to provide ethyl 6-iodo-1-(1-methoxy-3-methylbutan-2-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylate (623 mg, 60%).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionPotassium carbonate was added (978 mg, 7.08 mmol)
  3. stirringthe reaction mixture was stirred at 70° C. for 2 h
  4. temperatureThe reaction mixture was cooled down to room temperature
  5. customquenched with 1 N HCl
  6. customThe reaction mixture was partitioned between water (20 mL) and ethyl acetate (20 mL)
  7. extractionThe aqueous layer was extracted with ethyl acetate
  8. customthe organics were dried
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-2fa1c5dc513a41159369f90119a746f4
Source dataset
uspto-grants-2012_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08283361B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes