Lawesson's reagent → HCID 178501057, compound

HRID 1716508Notes

Reaction equation

HRID 1716508 reaction equation
[CH3:1][O:2][C:3]([C@H:5]1[CH2:10][CH2:9][C@H:8]([C:11](=O)[NH:12][CH2:13][C:14]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([Br:22])[N:17]=2)=O)[CH2:7][CH2:6]1)=[O:4].COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:33])=CC=1>O1CCCC1>[CH3:1][O:2][C:3]([C@H:5]1[CH2:10][CH2:9][C@H:8]([C:11]2[S:33][C:14]([C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([Br:22])[N:17]=3)=[CH:13][N:12]=2)[CH2:7][CH2:6]1)=[O:4]

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 178501160HCID 178501160, compound

Product 1

HCID 178501057HCID 178501057, compoundYield 82.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of trans-4-[2-(6-bromopyridin-2-yl)-2-oxoethylcarbamoyl]cyclohexanecarboxylic acid methyl ester (7.38 g, 19.3 mmol) obtained in Step 2 and a Lawesson reagent (8.20 g, 20.3 mmol) in tetrahydrofuran (120 ml) was heated at reflux for 2 hours in an Ar stream. After the reaction solution was concentrated, a saturated aqueous sodium bicarbonate was added and extracted with ethyl acetate. The organic layer was washed with a saturated sodium bicarbonate aqueous solution and dried over magnesium sulfate, and after concentrated, the residue was purified by flash chromatography on silica gel (n-hexane:ethyl acetate=1:1) and the title compound (6.1 g) was obtained.

Workup

  1. temperatureat reflux for 2 hours in an Ar stream
  2. concentrationAfter the reaction solution was concentrated
  3. additiona saturated aqueous sodium bicarbonate was added
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with a saturated sodium bicarbonate aqueous solution
  6. dry with materialdried over magnesium sulfate
  7. concentrationafter concentrated
  8. customthe residue was purified by flash chromatography on silica gel (n-hexane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-c42a456d052b44ef8e071b9acb57adb5
Source dataset
uspto-grants-2010_09
Patent number
US07803801B2

Reaction notes

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