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

HRID 2101358
Notes
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Reaction equation

HRID 2101358 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][C:18]1[CH:23]=[CH:22][C:21](B(O)O)=[CH:20][CH:19]=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>[CH3:17][C:18]1[CH:23]=[CH:22][C:21]([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:21]2[CH:22]=[CH:23][C:18]([CH3:17])=[CH:19][CH:20]=2)=[CH:20][CH:19]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 79799Tolylboronic acidHCID 577993827-bromo-8-iodo-2-isobutyl-[1,2,4]triazolo[4,3-a]pyridin-3(2H)-one

Product 1

HCID 577993737,8-bis(4-methylphenyl)-2-isobutyl-[1,2,4]triazolo[4,3-a]pyridin-3(2H)-oneYield 20.8%

Reagents, catalysts & solvents 3

HCID 178418397
HCID 178418397, compound
Catalyst
HCID 962WaterSolvent
HCID 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-methylphenylboronic 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 7 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, 0.027 mmol) as a pale yellow solid. MS: [M+H]+=372.

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-aa9112b31cca4a5583433bcbf717b324
Source dataset
uspto-grants-2009_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07572808B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes