Water → HCID 89996212, compound

HRID 1480869Notes

Reaction equation

HRID 1480869 reaction equation
[CH3:1][N:2]1[CH:6]=[CH:5][N:4]=[N:3]1.C([Li])CCC.Cl[C:13]1[N:18]=[C:17]([O:19][CH3:20])[C:16]([N+:21]([O-:23])=[O:22])=[CH:15][CH:14]=1.O>C1COCC1.CN(C=O)C.[Cl-].[Zn+2].[Cl-].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Pd].CCOC(C)=O>[CH3:20][O:19][C:17]1[C:16]([N+:21]([O-:23])=[O:22])=[CH:15][CH:14]=[C:13]([C:6]2[N:2]([CH3:1])[N:3]=[N:4][CH:5]=2)[N:18]=1

Participants

10

Reactant 4

HCID 962WaterHCID 1401191-Methyl-1H-1,2,3-triazoleHCID 107977036-Chloro-2-methoxy-3-nitropyridineHCID 178418339Butyllithium

Product 1

HCID 89996212HCID 89996212, compoundYield 41%

Reagents, catalysts & solvents 5

HCID 3007855ZincchlorideCatalystHCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 6228DimethylformamideSolvent2×HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

1-Methyl-1H-1,2,3-triazole (0.044 g, 0.530 mmol) was dissolved in THF (5.3 mL) and cooled to −78° C. n-Butyllithium solution in hexanes (0.25 mL, 0.636 mmol) was added dropwise and the solution was stirred for further 5 minutes before zinc chloride (3.18 mL, 1.591 mmol) was added. After 30 minutes at −78° C., the reaction mixture was diluted with DMF (2.1 mL), tetrakis(triphenylphosphine)palladium(O) (0.031 g, 0.027 mmol) and a solution of 6-chloro-2-methoxy-3-nitropyridine (0.1 g, 0.530 mmol) in DMF (0.53 mL) were added. The solution was stirred at 80° C. for 4 hours. After the mixture was cooled to room temperature, H2O and EtOAc were added and the phases were separated. The organic phase was washed with H2O, brine, dried (Na2SO4), filtered and the solvent was removed in vacuo. The residue was purified via Biotage silica gel column chromatography eluting with cyclohexane/EtOAc (99/1 to 50/50) to afford the title compound as a light yellow solid (51 mg, 41%).

Workup

  1. additionwas added dropwise
  2. additionwas added
  3. temperatureAfter the mixture was cooled to room temperature
  4. customthe phases were separated
  5. washThe organic phase was washed with H2O, brine
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. customthe solvent was removed in vacuo
  9. customThe residue was purified via Biotage silica gel column chromatography
  10. washeluting with cyclohexane/EtOAc (99/1 to 50/50)

Sources & evidence

ORD record
ord-eb296c4bebda4c328c509e13f833cbef
Source dataset
uspto-grants-2016_08
Patent number
US09409907B2

Reaction notes

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