Water → HCID 67508962, compound

HRID 623489Notes

Reaction equation

HRID 623489 reaction equation
Br[CH2:2][C:3]1[C:4]([O:13][CH2:14][C:15]([F:18])([F:17])[F:16])=[N:5][CH:6]=[C:7]([CH:12]=1)[C:8]([O:10][CH3:11])=[O:9].[C:19]([O-:22])(=[O:21])[CH3:20].[Na+].O>CC(N(C)C)=O>[C:19]([O:22][CH2:2][C:3]1[C:4]([O:13][CH2:14][C:15]([F:18])([F:17])[F:16])=[N:5][CH:6]=[C:7]([CH:12]=1)[C:8]([O:10][CH3:11])=[O:9])(=[O:21])[CH3:20]

Participants

5

Reactant 3

HCID 962WaterHCID 517045Sodium AcetateHCID 67508817HCID 67508817, compound

Product 1

HCID 67508962HCID 67508962, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of methyl 5-(bromomethyl)-6-(2,2,2-trifluoroethoxy)nicotinate (0.68 g, 2.07 mmol, Step-2) and sodium acetate (0.51 g, 6.20 mmol) in DMA (10 mL) is stirred at 130° C. for 2 hours. After cooling to room temperature, the reaction mixture is poured into water, extracted with ethyl acetate and dried over sodium sulfate and concentrated in vacuo. The residue is purified by column chromatography on silica gel eluting with n-Hexane/ethyl acetate (6:1) to give 0.35 g (56% yield) of the title compound as colorless oil.

Workup

  1. temperatureAfter cooling to room temperature
  2. extractionextracted with ethyl acetate
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue is purified by column chromatography on silica gel eluting with n-Hexane/ethyl acetate (6:1)

Sources & evidence

ORD record
ord-192d108b649b455c8404f73d1123458a
Source dataset
uspto-grants-2016_04
Patent number
US09302991B2

Reaction notes

Loading…