Potassium Carbonate → 2-[4-(3-Methanesulfonyl-propoxy)-2,6-dimethyl-phenyl]-[1,2,4]triazolo[1,5-a]pyridine-6-carboxylic acid methyl ester

HRID 2272826Notes

Reaction equation

HRID 2272826 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[CH:7][C:8]2[N:9]([N:11]=[C:12]([C:14]3[C:19]([CH3:20])=[CH:18][C:17]([OH:21])=[CH:16][C:15]=3[CH3:22])[N:13]=2)[CH:10]=1)=[O:4].[CH3:23][S:24]([CH2:27][CH2:28][CH2:29]OS(C1C=CC(C)=CC=1)(=O)=O)(=[O:26])=[O:25].C(=O)([O-])[O-].[K+].[K+]>C(#N)C.O>[CH3:1][O:2][C:3]([C:5]1[CH:6]=[CH:7][C:8]2[N:9]([N:11]=[C:12]([C:14]3[C:15]([CH3:22])=[CH:16][C:17]([O:21][CH2:29][CH2:28][CH2:27][S:24]([CH3:23])(=[O:26])=[O:25])=[CH:18][C:19]=3[CH3:20])[N:13]=2)[CH:10]=1)=[O:4]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 22732325(3-(Methylsulfonyl)propyl 4-methylbenzenesulfonateHCID 136992563Methyl 2-(4-hydroxy-2,6-dimethylphenyl)-[1,2,4]triazolo[1,5-a]pyridine-6-carboxylate

Product 1

HCID 1181299702-[4-(3-Methanesulfonyl-propoxy)-2,6-dimethyl-phenyl]-[1,2,4]triazolo[1,5-a]pyridine-6-carboxylic acid methyl esterYield 70.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 2-(4-hydroxy-2,6-dimethyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridine-6-carboxylic acid methyl ester (0.2 g, 0.673 mmol) in acetonitrile (5 mL) is added toluene-4-sulfonic acid 3-methanesulfonyl-propyl ester (0.196 g, 0.673 mmol) and potassium carbonate (0.278 g, 2.019 mmol) at room temperature and the reaction mixture is heated at 100° C. for 16 hours. The reaction mixture is diluted with water (10 mL) and extracted with EtOAc (2×20 mL). The combined organic extracts are washed with water (10 mL), brine (10 mL), dried over anhydrous Na2SO4, filtered, and evaporated to dryness. The crude material is purified by silica gel chromatography (combiflash purifier 24 g redisep column) and is eluted with 40-60% EtOAc in hexane to give the title compound as a light yellow solid (198 mg, 70%). LCMS m/z 418 [M+H]+.

Workup

  1. extractionextracted with EtOAc (2×20 mL)
  2. washThe combined organic extracts are washed with water (10 mL), brine (10 mL)
  3. dry with materialdried over anhydrous Na2SO4
  4. filtrationfiltered
  5. customevaporated to dryness
  6. customThe crude material is purified by silica gel chromatography (combiflash purifier 24 g redisep column)
  7. washis eluted with 40-60% EtOAc in hexane

Sources & evidence

ORD record
ord-7890c147dc31499ab2d4ae37c5ea1c02
Source dataset
uspto-grants-2015_09
Patent number
US09120793B2

Reaction notes

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