Dimethylformamide → HCID 89485502, compound

HRID 2401693Notes

Reaction equation

HRID 2401693 reaction equation
F[C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[C:8]1[O:9][C:10]2[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][C:11]=2[CH:12]=1.[Na].[CH3:22][SH:23].CN(C=O)C>O>[CH3:22][S:23][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[C:8]1[O:9][C:10]2[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][C:11]=2[CH:12]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 45051789Methylmercaptan sodium2×HCID 86680834HCID 86680834, compound

Product 1

HCID 89485502HCID 89485502, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 0.30 g of 3-fluoro-4-[5-(trifluoromethyl)benzofuran-2-yl]pyridine, 75 mg of methyl mercaptan sodium salt and 4 ml of DMF was stirred under ice-cooling for 1 hour. To this mixture was added 37 mg of methyl mercaptan sodium salt, and the mixture was stirred under ice-cooling for further 1 hour. Water was added to the reaction mixture, and the mixture was extracted twice with ethyl acetate. The organic layers were combined and washed with water and saturated brine and dried over magnesium sulfate, then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 0.31 g of 3-methylthio-4-[5-(trifluoromethyl)benzofuran-2-yl]pyridine (hereinafter, referred to as “Present Active Compound 11”).

Workup

  1. temperaturecooling for 1 hour
  2. stirringthe mixture was stirred under ice-
  3. temperaturecooling for further 1 hour
  4. extractionthe mixture was extracted twice with ethyl acetate
  5. washwashed with water and saturated brine
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ae0b5ef7b5374b1d8bd10be43fdc56e8
Source dataset
uspto-grants-2014_08
Patent number
US08796306B2

Reaction notes

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