Methyl iodide → Ethyl 6-[(1-methoxy-2-methylindolizin-3-yl)carbonyl]-1-methyl-4-oxo-1,4-dihydroquinoline-3-carboxylate

HRID 535464Notes

Reaction equation

HRID 535464 reaction equation
[C:1](=O)([O-])[O-].[K+].[K+].CI.[CH3:9][O:10][C:11]1[C:12]([CH3:38])=[C:13]([C:20]([C:22]2[CH:23]=[C:24]3[C:29](=[CH:30][CH:31]=2)[NH:28][CH:27]=[C:26]([C:32]([O:34][CH2:35][CH3:36])=[O:33])[C:25]3=[O:37])=[O:21])[N:14]2[C:19]=1[CH:18]=[CH:17][CH:16]=[CH:15]2>CN(C=O)C>[CH3:9][O:10][C:11]1[C:12]([CH3:38])=[C:13]([C:20]([C:22]2[CH:23]=[C:24]3[C:29](=[CH:30][CH:31]=2)[N:28]([CH3:1])[CH:27]=[C:26]([C:32]([O:34][CH2:35][CH3:36])=[O:33])[C:25]3=[O:37])=[O:21])[N:14]2[C:19]=1[CH:18]=[CH:17][CH:16]=[CH:15]2

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 66653275HCID 66653275, compound

Product 1

HCID 66653206Ethyl 6-[(1-methoxy-2-methylindolizin-3-yl)carbonyl]-1-methyl-4-oxo-1,4-dihydroquinoline-3-carboxylateYield 93.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

3.8 g (27.89 mmol) of potassium carbonate and 1.74 ml (27.89 mmol) of methyl iodide are added, at ambient temperature under an inert atmosphere, to 10 g (23.24 mmol) of ethyl 6-[(1-methoxy-2-methylindolizin-3-yl)carbonyl]-4-oxo-1,4-dihydroquinoline-3-carboxylate in 100 ml of DMF. The reaction medium is heated at 90° C. for 1 h 30. The reaction medium is filtered through talc, diluted with dichloromethane, and then washed with water. The organic phase is dried with sodium sulphate and then concentrated under reduced pressure. The residue obtained is purified by silica gel column chromatography, elution being carried out with a dichloromethane/methanol (90/10) mixture. 9.1 g of a yellow solid are obtained.

Workup

  1. filtrationThe reaction medium is filtered through talc
  2. additiondiluted with dichloromethane
  3. washwashed with water
  4. dry with materialThe organic phase is dried with sodium sulphate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue obtained
  7. customis purified by silica gel column chromatography, elution

Sources & evidence

ORD record
ord-cb75e6fd84224d45a0b81e4b0e919d49
Source dataset
uspto-grants-2014_10
Patent number
US08859544B2

Reaction notes

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