Iodoethane → HCID 67133798, compound

HRID 1949157Notes

Reaction equation

HRID 1949157 reaction equation
[Na].C([O:4][C:5]([C:7]1[C:8]([S:22][CH2:23][CH2:24]C(OCC)=O)=[N:9][C:10]2[C:15]([C:16]=1[CH3:17])=[CH:14][CH:13]=[C:12]([C:18]([F:21])([F:20])[F:19])[CH:11]=2)=[O:6])C.ICC>CO>[CH2:23]([S:22][C:8]1[C:7]([C:5]([OH:6])=[O:4])=[C:16]([CH3:17])[C:15]2[C:10](=[CH:11][C:12]([C:18]([F:21])([F:19])[F:20])=[CH:13][CH:14]=2)[N:9]=1)[CH3:24]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 5360545SodiumHCID 68507420HCID 68507420, compound

Product 1

HCID 67133798HCID 67133798, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

400 mg (17.4 mmol) sodium were added slowly to MeOH (50 ml) and the solution was stirred for 5 min at RT. Then a solution of 800 mg (2.0 mmol) 2-(3-ethoxy-3-oxopropylthio)-4-methyl-7-(trifluoromethyl)quinoline-3-carboxylic acid ethyl ester (precursor VVV07) in MeOH (10 ml) was added at RT. The reaction solution was then heated for 30 min at 70° C. After cooling to RT 488 μl (6.0 mmol) 1-iodethane were added and the mixture was stirred for 2 h at RT. Then the mixture was concentrated to small volume under vacuum and the residue was taken up with EE. It was washed with water and the aqueous phase was extracted with EE. The combined organic phases were washed with brine, dried over MgSO4, filtered and concentrated to small volume under vacuum. 391 mg (1.2 mmol, 62%) 2-(ethylthio)-4-methyl-7-(trifluoromethyl)quinoline-3-carboxylic acid were obtained as the residue, which was reacted further with no additional purification.

Workup

  1. temperatureThe reaction solution was then heated for 30 min at 70° C
  2. additionwere added
  3. stirringthe mixture was stirred for 2 h at RT
  4. concentrationThen the mixture was concentrated to small volume under vacuum
  5. washIt was washed with water
  6. extractionthe aqueous phase was extracted with EE
  7. washThe combined organic phases were washed with brine
  8. dry with materialdried over MgSO4
  9. filtrationfiltered
  10. concentrationconcentrated to small volume under vacuum

Sources & evidence

ORD record
ord-caadeb901a8f4d2eb02743b67116381d
Source dataset
uspto-grants-2013_03
Patent number
US08399673B2

Reaction notes

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