Methyl iodide → HCID 59415893, compound

HRID 2061878Notes

Reaction equation

HRID 2061878 reaction equation
[I:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]([C@@H:12]1[CH2:16][CH2:15][NH:14][CH2:13]1)[CH:7]=[C:6]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[C:5]2=[O:22].IC.[C:25](=O)([O-])[O-].[K+].[K+]>C1COCC1>[I:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]([C@@H:12]1[CH2:16][CH2:15][N:14]([CH3:25])[CH2:13]1)[CH:7]=[C:6]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[C:5]2=[O:22]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 59415865HCID 59415865, compound2×

Product 1

HCID 59415893HCID 59415893, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of (R)-ethyl 6-iodo-4-oxo-1-(pyrrolidin-3-yl)-1,4-dihydroquinoline-3-carboxylate (Intermediate 110, 282 mg, 0.68 mmol, 1 equiv.) in THF (7 mL) was added iodomethane (0.0471 mL, 0.75 mmol, 1.1 equiv.) followed by potassium carbonate (378 mg, 2.74 mmol, 4 equiv.). This was stirred at 60° C. for 1 d. The reaction mixture was cooled to room temperature and partitioned between ethyl acetate (10 mL) and water (10 mL). The aqueous layer was extracted with ethyl acetate (2×10 mL), and the organics were concentrated to provide (R)-ethyl 6-iodo-1-(1-methylpyrrolidin-3-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylate as a light yellow solid (282 mg, >99%).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. custompartitioned between ethyl acetate (10 mL) and water (10 mL)
  3. extractionThe aqueous layer was extracted with ethyl acetate (2×10 mL)
  4. concentrationthe organics were concentrated

Sources & evidence

ORD record
ord-0c8d9aa35a6d4626ab14d8959a8694e0
Source dataset
uspto-grants-2012_10
Patent number
US08283361B2

Reaction notes

Loading…