1-Bromo-3-methylbutane → 7,8-bis(4-chlorophenyl)-2-isopentyl-[1,2,4]triazolo[4,3-a]pyridin-3(2H)-one

HRID 2101372Notes

Reaction equation

HRID 2101372 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][N:11]3[C:14](=[O:17])[NH:15][N:16]=[C:10]3[C:9]=2[C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=2)=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].Br[CH2:32][CH2:33][CH:34]([CH3:36])[CH3:35]>CN(C=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][N:11]3[C:14](=[O:17])[N:15]([CH2:32][CH2:33][CH:34]([CH3:36])[CH3:35])[N:16]=[C:10]3[C:9]=2[C:18]2[CH:19]=[CH:20][C:21]([Cl:24])=[CH:22][CH:23]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 78911-Bromo-3-methylbutaneHCID 11430Potassium CarbonateHCID 577993867,8-Bis(4-chlorophenyl)[1,2,4]triazolo[4,3-a]pyridin-3(2H)-one

Product 1

HCID 577993817,8-bis(4-chlorophenyl)-2-isopentyl-[1,2,4]triazolo[4,3-a]pyridin-3(2H)-oneYield 45%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a stirring mixture of 7,8-bis(4-chlorophenyl)-[1,2,4]triazolo[4,3-a]pyridin-3(2H)-one (50 mg, 0.14 mmol) and K2CO3 (40 mg, 0.28 mmol) in DMF (0.47 mL) at 20° C. was added 1-bromo-3-methylbutane (40 mg, 0.28 mmol). The resulting reaction mixture was heated at 80° C. for 60 min. Analysis by HPLC/MS indicated that starting material had been consumed. The reaction mixture was brought to room temperature, diluted with water, and extracted twice with diethyl ether. The combined organic extract was washed with saturated aqueous NaHCO3 solution, then brine, then dried (MgSO4), filtered, and concentrated under reduced pressure. The crude product was purified by reverse phase preparative HPLC (acetonitrile-water-TFA) to isolate the title compound (27 mg, 0.063 mmol) as a yellow oil. MS: [M+H]+=426.

Workup

  1. customThe resulting reaction mixture
  2. customhad been consumed
  3. customwas brought to room temperature
  4. additiondiluted with water
  5. extractionextracted twice with diethyl ether
  6. extractionThe combined organic extract
  7. washwas washed with saturated aqueous NaHCO3 solution
  8. dry with materialbrine, then dried (MgSO4)
  9. filtrationfiltered
  10. concentrationconcentrated under reduced pressure
  11. customThe crude product was purified by reverse phase preparative HPLC (acetonitrile-water-TFA)

Sources & evidence

ORD record
ord-1962ed31c40d4ed08eb386a6ed6084f2
Source dataset
uspto-grants-2009_08
Patent number
US07572808B2

Reaction notes

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