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

HRID 2101360Notes

Reaction equation

HRID 2101360 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]=1I.[CH3:17][O:18][C:19]1[CH:24]=[CH:23][C:22](B(O)O)=[CH:21][CH:20]=1.[C:28]([O-:31])([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>[CH3:17][O:18][C:19]1[CH:24]=[CH:23][C:22]([C:2]2[CH:7]=[CH:6][N:5]3[C:8](=[O:15])[N:9]([CH2:11][CH:12]([CH3:14])[CH3:13])[N:10]=[C:4]3[C:3]=2[C:19]2[CH:24]=[CH:23][C:22]([O:31][CH3:28])=[CH:21][CH:20]=2)=[CH:21][CH:20]=1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 201262(4-Methoxyphenyl)boronic acidHCID 577993827-bromo-8-iodo-2-isobutyl-[1,2,4]triazolo[4,3-a]pyridin-3(2H)-one

Product 1

HCID 577994247,8-bis(4-methoxyphenyl)-2-isobutyl-[1,2,4]triazolo[4,3-a]pyridin-3(2H)-oneYield 19.2%

Reagents, catalysts & solvents 3

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

Conditions

Temperature
200 °C

Procedure

To a stirring, degassed mixture of 7-bromo-8-iodo-2-isobutyl-[1,2,4]triazolo[4,3-a]pyridin-3(2H)-one (50 mg, 0.13 mmol), 4-methoxyphenylboronic acid (40 mg, 0.28 mmol), and tetrakis(triphenylphosphine)palladium (7 mg, 0.006 mmol) in dioxane (1.0 mL) at 20° C. was added K2CO3 (40 mg, 0.25 mmol) in water (0.3 mL). The resulting reaction mixture was heated in a microwave reactor at 200° C. for 20 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 the title compound (10 mg, 0.025 mmol) as a pale yellow solid. MS: [M+H]+=404.

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-319628f0e2c449de84a3e7c7c6f6bece
Source dataset
uspto-grants-2009_08
Patent number
US07572808B2

Reaction notes

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