2-Aminopyridine → 1171897-93-0

HRID 1878626Notes

Reaction equation

HRID 1878626 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6](Br)[C:7]=1[CH2:8][CH2:9][CH2:10][OH:11].NC1C=CC=CN=1.C[O-].[Na+].C([O-])(O)=O.[Na+]>COCCOC.[Cu]Cl>[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]2[O:11][CH2:10][CH2:9][CH2:8][C:7]=12

Participants

7

Reactant 4

HCID 104392-AminopyridineHCID 516892Sodium BicarbonateHCID 10942334Sodium MethoxideHCID 68761658HCID 68761658, compound

Product 1

HCID 687379191171897-93-0

Reagents, catalysts & solvents 2

HCID 62652Cuprous chlorideCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

To a solution of 3-(3,5-dibromo-pyridin-4-yl)-propan-1-ol (1 eq, 4.41 mmol, 1.3 g) in DME (8 ml) is added copper (I) chloride (0.05 eq, 0.22 mmol, 22 mg), 2-aminopyridine (0.05 eq, 0.22 mmol, 21 mg), and NaOMe (5.4M in MeOH, 1.5 eq, 6.61 mmol, 1.22 ml). The resulting mixture is heated using microwave radiation at 70° C. for 20 h. Then sat. aqueous NaHCO3 solution is added, and the mixture is extracted with EtOAc. The organic layer is dried with MgSO4, filtered, and concentrated in vacuo. The crude product is purified using column chromatography (hexane/EtOAc) to give the title compound; [M+H]+=214/216.

Workup

  1. temperatureThe resulting mixture is heated
  2. customat 70° C.
  3. customfor 20 h
  4. extractionthe mixture is extracted with EtOAc
  5. dry with materialThe organic layer is dried with MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude product is purified

Sources & evidence

ORD record
ord-4d9156f88a8946e79b6de3b645865391
Source dataset
uspto-grants-2012_11
Patent number
US08314112B2

Reaction notes

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