tert-Butanol → HCID 86708203, compound

HRID 533607Notes

Reaction equation

HRID 533607 reaction equation
[CH2:1]([S:3][C:4]1[CH:21]=[CH:20][CH:19]=[CH:18][C:5]=1[C:6]([NH:8][C:9]1[C:10]([NH:16][CH3:17])=[N:11][CH:12]=[C:13]([CH3:15])[CH:14]=1)=O)[CH3:2].P([O-])([O-])([O-])=O.[K+].[K+].[K+].C(O)(C)(C)C>O>[CH2:1]([S:3][C:4]1[CH:21]=[CH:20][CH:19]=[CH:18][C:5]=1[C:6]1[N:16]([CH3:17])[C:10]2=[N:11][CH:12]=[C:13]([CH3:15])[CH:14]=[C:9]2[N:8]=1)[CH3:2]

Participants

5

Reactant 3

HCID 6386tert-ButanolHCID 62657Potassium Phosphate, TribasicHCID 67981213HCID 67981213, compound

Product 1

HCID 86708203HCID 86708203, compoundYield 20.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
82 °C

Procedure

A mixture of 2-ethylsulfanyl-N-(5-methyl-2-methylaminopyridin-3-yl)-benzamide (1.40 g), tripotassium phosphate (1.97 g), and tert-butanol (10 ml) was stirred under reflux at 82° C. for 2 hours. Into the reaction mixture cooled to room temperature, water was poured, and extracted with ethyl acetate. The organic layer was dried over magnesium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography to give 0.27 g of 2-(2-ethylsulfanylphenyl)-3,6-dimethyl-3H-imidazo[4,5-b]pyridine (hereinafter referred to as Present Compound 39).

Workup

  1. temperatureInto the reaction mixture cooled to room temperature
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-7cef02387d1a47ae8f3e24c29d8c75ee
Source dataset
uspto-grants-2014_10
Patent number
US08853238B2

Reaction notes

Loading…