Ethyl Acetate → 5-(4-Methoxyphenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-amine

HRID 336399Notes

Reaction equation

HRID 336399 reaction equation
Br[C:2]1[N:7]2[N:8]=[C:9]([NH2:11])[N:10]=[C:6]2[CH:5]=[CH:4][CH:3]=1.[C:12]([O:15][CH2:16][CH3:17])(=O)C>C(#N)C.C(=O)([O-])[O-].[Na+].[Na+].Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:12][O:15][C:16]1[CH:17]=[CH:5][C:4]([C:2]2[N:7]3[N:8]=[C:9]([NH2:11])[N:10]=[C:6]3[CH:5]=[CH:4][CH:3]=2)=[CH:3][CH:2]=1

Participants

6

Reactant 2

HCID 8857Ethyl AcetateHCID 252159395-Bromo-[1,2,4]triazolo[1,5-a]pyridin-2-amine

Product 1

HCID 591864185-(4-Methoxyphenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-amineYield 83%

Reagents, catalysts & solvents 3

HCID 178418476HCID 178418476, compoundCatalystHCID 6342AcetonitrileSolventHCID 10340Sodium CarbonateSolvent

Procedure

A solution of 5-bromo-[1,2,4]triazolo[1,5-a]pyridin-2-amine (1.5 g, 7.0 mmol, 1 equiv) and bis(triphenylphosphine)palladium(II) chloride (500 mg, 0.7 mmol 0.1 equiv) in acetonitrile (10 mL) and 1M aqueous sodium carbonate solution (10 mL) was heated at 120° C. for 3 min in the microwave. The reaction mixture was diluted with ethyl acetate, and the resulting solution was washed water (2×) and saturated aqueous sodium chloride solution. Purification by flash column chromatography (2→10% methanol in dichloromethane) provided product (1.4 g, 83%). 1H NMR (400 MHz, CDCl3), δ: 7.90 (d, 2H), 7.48 (m, 1H), 7.39 (m, 1H), 7.05 (d, 2H), 6.88 (dd, 1H), 4.25 (s, 2H); ES-MS m/z 241.0.

Workup

  1. washthe resulting solution was washed water (2×) and saturated aqueous sodium chloride solution
  2. customPurification by flash column chromatography (2→10% methanol in dichloromethane)

Sources & evidence

ORD record
ord-8bd3dda40c6e45419dbadfa787002be6
Source dataset
uspto-grants-2014_11
Patent number
US08889673B2

Reaction notes

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