Water → HCID 67508999, compound

HRID 715347Notes

Reaction equation

HRID 715347 reaction equation
[CH3:1][C:2]1[C:3]([O:11][CH2:12][C:13]([F:16])([F:15])[F:14])=[N:4][CH:5]=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8].IC.[C:19](=O)([O-])[O-].[K+].[K+].O>CC(N(C)C)=O>[CH3:1][C:2]1[C:3]([O:11][CH2:12][C:13]([F:16])([F:14])[F:15])=[N:4][CH:5]=[C:6]([CH:10]=1)[C:7]([O:9][CH3:19])=[O:8]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 67509860HCID 67509860, compound

Product 1

HCID 67508999HCID 67508999, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

A mixture of 5-methyl-6-(2,2,2-trifluoroethoxy)nicotinic acid (3.08 g, 13.1 mmol, Step-1 of Amine-2), iodomethane (0.983 ml, 15.72 mmol) and potassium carbonate (5.43 g, 39.3 mmol) in DMA (40 ml) is stirred at rt for 2 hours. The reaction mixture is poured into water (200 mL) and extracted with n-hexane/EtOAc (1:10, 500 mL). The organic layer is washed with 2M hydrochloric acid (300 mL×2) and dried over sodium sulfate. After filtration, the filtrate is concentrated in vacuo. The residue is purified by column chromatography on silica gel eluting with n-hexane/EtOAc (5:1) to give 2.87 g (88% yield) of the title compound as white solid.

Workup

  1. extractionextracted with n-hexane/EtOAc (1:10, 500 mL)
  2. washThe organic layer is washed with 2M hydrochloric acid (300 mL×2)
  3. dry with materialdried over sodium sulfate
  4. filtrationAfter filtration
  5. concentrationthe filtrate is concentrated in vacuo
  6. customThe residue is purified by column chromatography on silica gel eluting with n-hexane/EtOAc (5:1)

Sources & evidence

ORD record
ord-7f8b050cc8ce41b0923734fe5ed24a4f
Source dataset
uspto-grants-2015_11
Patent number
US09187475B2

Reaction notes

Loading…