Dimethylformamide → HCID 80153386, compound

HRID 1477625Notes

Reaction equation

HRID 1477625 reaction equation
CN(C)C=O.[OH:6][CH2:7][C:8]1[CH:17]=[CH:16][C:11]([C:12]([O:14][CH3:15])=[O:13])=[CH:10][N:9]=1.FC(F)(F)S(O[CH2:24][C:25]([F:28])([F:27])[F:26])(=O)=O.[H-].[Na+]>C(OCC)(=O)C.O>[F:26][C:25]([F:28])([F:27])[CH2:24][O:6][CH2:7][C:8]1[CH:17]=[CH:16][C:11]([C:12]([O:14][CH3:15])=[O:13])=[CH:10][N:9]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 803662,2,2-Trifluoroethyl trifluoromethanesulfonateHCID 7894146-Hydroxymethyl-nicotinic acid methyl ester

Product 1

HCID 80153386HCID 80153386, compoundYield 23%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To an N,N-dimethylformamide solution (10 mL) of methyl 6-(hydroxymethyl)nicotinate (500 mg, 2.99 mmol) and 2,2,2-trifluoroethyl trifluoromethanesulfonate (518 μL, 3.59 mmol), sodium hydride (179 mg, 4.49 mmol) was added at 0° C. and the resultant mixture was stirred at room temperature for 4 hours. After completion of the reaction, water was added to the reaction solution and extraction from the resultant mixture with ethyl acetate was performed. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=5/1) to obtain the title compound (171 mg, yield 23%).

Workup

  1. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  2. concentrationconcentrated under reduced pressure
  3. customThe obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=5/1)

Sources & evidence

ORD record
ord-7ffc009851854679b5d284c590ab886c
Source dataset
uspto-grants-2016_08
Patent number
US09403798B2

Reaction notes

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