Dimethylformamide → HCID 86708217, compound

HRID 533636Notes

Reaction equation

HRID 533636 reaction equation
F[C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[CH:4][C:3]=1[C:12]1[S:13][C:14]2[C:19]([N:20]=1)=[CH:18][C:17]([C:21]([F:24])([F:23])[F:22])=[CH:16][N:15]=2.[CH3:25]N(C=O)C.[CH3:30][S-:31].[Na+]>O>[CH2:30]([S:31][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[CH:4][C:3]=1[C:12]1[S:13][C:14]2[C:19]([N:20]=1)=[CH:18][C:17]([C:21]([F:24])([F:23])[F:22])=[CH:16][N:15]=2)[CH3:25]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 4378561Sodium methanethiolateHCID 86708218HCID 86708218, compound

Product 1

HCID 86708217HCID 86708217, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 2-[2-fluoro-4-(trifluoromethyl)phenyl]-6-(trifluoromethyl)thiazolo[5,4-b]pyridine (0.18 g) and DMF (2 ml), sodium thiomethoxide (63 mg) was added under ice-cooling, and stirred at room temperature for 4 hours. Into the reaction mixture, water was poured, and extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography to give 0.11 g of 2-[2-ethylsulfanyl-4-(trifluoromethyl)phenyl]-6-(trifluoromethyl)thiazolo[5,4-b]pyridine (hereinafter referred to as Present Compound 267).

Workup

  1. additionwas added under ice-
  2. temperaturecooling
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-7cfd7e3a0de1488c9afc01b9aa8cf50c
Source dataset
uspto-grants-2014_10
Patent number
US08853238B2

Reaction notes

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