Potassium Iodide → 2-(2-Benzyloxy-ethoxy)-4-methyl-6-(3-trifluoromethyl-phenyl)-nicotinic acid methyl ester

HRID 1692393

Reaction equation

HRID 1692393 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:6](=[O:22])[NH:7][C:8]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:21])([F:20])[F:19])[CH:13]=2)=[CH:9][C:10]=1[CH3:11])=[O:4].C(=O)([O-])[O-].[Cs+].[Cs+].[I-].[K+].Br[CH2:32][CH2:33][O:34][CH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1>CS(C)=O>[CH3:1][O:2][C:3](=[O:4])[C:5]1[C:10]([CH3:11])=[CH:9][C:8]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:21])([F:19])[F:20])[CH:13]=2)=[N:7][C:6]=1[O:22][CH2:32][CH2:33][O:34][CH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 10796Cesium carbonateHCID 73833Benzene, ((2-bromoethoxy)methyl)-HCID 574411304-Methyl-2-oxo-6-(3-trifluoromethyl-phenyl)-1,2-dihydro-pyridine-3-carboxylic acid methyl ester

Product 1

HCID 669015852-(2-Benzyloxy-ethoxy)-4-methyl-6-(3-trifluoromethyl-phenyl)-nicotinic acid methyl esterYield 82%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A solution of 0.62 g (2.0 mmol) of 4-methyl-2-oxo-6-(3-trifluoromethyl-phenyl)-1,2-dihydro-pyridine-3-carboxylic acid methyl ester in 10 ml of DMSO was treated at RT with 1.947 g (6.0 mmol) of cesium carbonate and 0.066 g (0.4 mmol) of potassium iodide. 0.38 ml=0.514 g (2.4 mmol) of (2-bromo-ethoxymethyl)-benzene was added drop by drop and the reaction mixture was stirred for 16 hours at RT. It was then poured into crashed ice and extracted three times with CH2Cl2; the organic phases were washed with water, dried over magnesium sulfate, filtered and evaporated. The residue was purified by flash column chromatography (heptane/EtOAc 1:0 to 1:1) to give 0.73 g (82%) of the title compound as light yellow oil. MS: 446.2 (MH+).

Workup

  1. additionIt was then poured
  2. extractionextracted three times with CH2Cl2
  3. washthe organic phases were washed with water
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified by flash column chromatography (heptane/EtOAc 1:0 to 1:1)

Sources & evidence

ORD record
ord-56a5f4d45e8d48aab6e12a7b00c199b0
Source dataset
uspto-grants-2012_04
Patent number
US08153805B2

Linked notes

Loading…