Potassium Carbonate → 2-isobutyl-7-(4-methoxyphenyl)-8-p-tolyl-[1,2,4]triazolo[4,3-a]pyridin-3(2H)-one

HRID 2101367Notes

Reaction equation

HRID 2101367 reaction equation
Br[C:2]1[CH:7]=[CH:6][N:5]2[C:8](=[O:15])[N:9]([CH2:11][CH:12]([CH3:14])[CH3:13])[N:10]=[C:4]2[C:3]=1[C:16]1[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][CH:17]=1.[CH3:23][O:24][C:25]1[CH:30]=[CH:29][C:28](B(O)O)=[CH:27][CH:26]=1.C([O-])([O-])=O.[K+].[K+]>O1CCOCC1.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:11]([N:9]1[C:8](=[O:15])[N:5]2[CH:6]=[CH:7][C:2]([C:28]3[CH:29]=[CH:30][C:25]([O:24][CH3:23])=[CH:26][CH:27]=3)=[C:3]([C:16]3[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][CH:17]=3)[C:4]2=[N:10]1)[CH:12]([CH3:14])[CH3:13]

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 201262(4-Methoxyphenyl)boronic acidHCID 577994297-bromo-2-isobutyl-8-p-tolyl-[1,2,4]triazolo[4,3-a]pyridin-3(2H)-one

Product 1

HCID 577993912-isobutyl-7-(4-methoxyphenyl)-8-p-tolyl-[1,2,4]triazolo[4,3-a]pyridin-3(2H)-oneYield 90.3%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
150 °C

Procedure

To a stirring, degassed mixture of 7-bromo-2-isobutyl-8-p-tolyl-[1,2,4]triazolo[4,3-a]pyridin-3(2H)-one (0.015 g, 0.04 mmol), 4-methoxyphenylboronic acid (0.026 g, 0.17 mmol), and tetrakis(triphenylphosphine)palladium (2.5 mg, 0.002 mmol) in dioxane (0.3 mL) at 20° C. was added K2CO3 (0.024 g, 0.17 mmol) in water (0.11 mL). The resulting reaction mixture was heated in a microwave reactor at 150° C. for 10 min under argon. Analysis by HPLC/MS indicated that starting material had been consumed. The reaction mixture was brought to room temperature and was concentrated under reduced pressure. The crude product was purified by reverse phase preparative HPLC (acetonitrile-water-TFA) to isolate 14 mg of the title compound as a yellow solid. MS: [M+H]+=389.

Workup

  1. customTo a stirring, degassed
  2. customThe resulting reaction mixture
  3. customhad been consumed
  4. customwas brought to room temperature
  5. concentrationwas concentrated under reduced pressure
  6. customThe crude product was purified by reverse phase preparative HPLC (acetonitrile-water-TFA)

Sources & evidence

ORD record
ord-7a162dd680304990ba79ac95be905698
Source dataset
uspto-grants-2009_08
Patent number
US07572808B2

Reaction notes

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