Isopropanol → 6-(Propan-2-yl)pyridin-2-amine

HRID 1454808Notes

Reaction equation

HRID 1454808 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4](Br)[N:3]=1.[CH:9]([Zn]C(C)C)([CH3:11])[CH3:10].CC(O)C>O1CCOCC1.C1(C)C=CC=CC=1>[CH:9]([C:4]1[N:3]=[C:2]([NH2:1])[CH:7]=[CH:6][CH:5]=1)([CH3:11])[CH3:10]

Participants

6

Reactant 3

HCID 3776IsopropanolHCID 3008092-Amino-6-bromopyridineHCID 178461828HCID 178461828, compound

Product 1

HCID 217255966-(Propan-2-yl)pyridin-2-amine

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 312751,4-DioxaneSolvent

Procedure

2-Amino-6-bromopyridine (2 g) was dissolved in dioxane (50 mL), and at 0° C. under an argon athmosphere 1,3-bis(diphenylphosphino)propane nickel (II) chloride (0.627 g) was added followed by diisopropyl zinc (23.12 mL of a 1M solution in toluene, via syringe over 30 minutes). The mixture was allowed to reflux for 15 h, poured into 2-propanol, which was then concentrated in vacuo. The residue was partitioned between AcOEt and saturated aqueous NH4Cl solution, the layers were separated and the organic layer dried over Na2SO4, filtered and evaporated. The residue was purified by flash chromatography (methylene chloride/methanol 95:5) to give 6-isopropyl-pyridin-2-ylamine as light brown oil (0.48 g). MS (EI): 136.1 (M+).

Workup

  1. additionat 0° C. under an argon athmosphere 1,3-bis(diphenylphosphino)propane nickel (II) chloride (0.627 g) was added
  2. temperatureto reflux for 15 h
  3. concentrationwas then concentrated in vacuo
  4. customThe residue was partitioned between AcOEt and saturated aqueous NH4Cl solution
  5. customthe layers were separated
  6. dry with materialthe organic layer dried over Na2SO4
  7. filtrationfiltered
  8. customevaporated
  9. customThe residue was purified by flash chromatography (methylene chloride/methanol 95:5)

Sources & evidence

ORD record
ord-b802407e8fc249c0b3523f0144b00c4d
Source dataset
uspto-grants-2009_01
Patent number
US07482341B2

Reaction notes

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