Ethanol → HCID 118113476, compound

HRID 713674Notes

Reaction equation

HRID 713674 reaction equation
[C]=O.Cl[C:4]1[CH:5]=[C:6]([S:25]([CH2:28][CH3:29])(=[O:27])=[O:26])[C:7]([C:10]([N:12]([CH3:24])[C:13]2[CH:18]=[CH:17][C:16]([S:19][C:20]([F:23])([F:22])[F:21])=[CH:15][CH:14]=2)=[O:11])=[N:8][CH:9]=1.[C:30]([O-:33])(=[O:32])C.[Na+].[CH2:35](O)[CH3:36]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2].O>[CH2:28]([S:25]([C:6]1[C:7]([C:10](=[O:11])[N:12]([CH3:24])[C:13]2[CH:18]=[CH:17][C:16]([S:19][C:20]([F:23])([F:21])[F:22])=[CH:15][CH:14]=2)=[N:8][CH:9]=[C:4]([CH:5]=1)[C:30]([O:33][CH2:35][CH3:36])=[O:32])(=[O:26])=[O:27])[CH3:29]

Participants

8

Reactant 4

HCID 702EthanolHCID 517045Sodium AcetateHCID 118113312HCID 118113312, compoundHCID 178418416HCID 178418416, compound2×

Product 1

HCID 118113476HCID 118113476, compound

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalyst2×HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)Catalyst2×HCID 962WaterSolvent

Conditions

Temperature
110 °C

Procedure

Carbon monoxide at 10 atm was introduced to a mixture of 1.07 g of 5-chloro-3-ethylsulfonyl-N-methyl-N-(4-trifluoromethylsulfanylphenyl)picolinamide (Compound of Present Invention 118), 6 mg of palladium(II) acetate, 80 mg of 1,1′-bis(diphenylphosphino)ferrocene, 410 mg of sodium acetate and 20 ml of ethanol, and the mixture was stirred at 110° C. for 3 hours. 6 mg of palladium(II) acetate and 80 mg of 1,1′-bis(diphenylphosphino)ferrocene were added to the cooled reaction mixture, then carbon monoxide at 10 atm was introduced, and the mixture was stirred at 130° C. for 3 hours. The cooled reaction mixture was poured to water, and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and then concentrated under reduced pressure, and the resulting residue was applied to a silica gel column chromatography to obtain 0.96 g of ethyl 5-ethylsulfonyl-6-[methyl-(4-trifluoromethylsulfanylphenyl) carbamoyl]nicotinate (hereinafter, referred to as Compound of Present Invention 125).

Workup

  1. stirringthe mixture was stirred at 130° C. for 3 hours
  2. customThe cooled reaction mixture
  3. extractionthe mixture was extracted with ethyl acetate
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c7a4c4ebda594c92b21e0e94449ffa12
Source dataset
uspto-grants-2015_11
Patent number
US09185910B2

Reaction notes

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