2,6-Dibromopyridine → 6-Bromo-N-(cyclopropylmethyl)pyridin-2-amine

HRID 993238Notes

Reaction equation

HRID 993238 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Br:8])[N:3]=1.[CH:9]1([CH2:12][NH2:13])[CH2:11][CH2:10]1>CCN(C(C)C)C(C)C>[Br:8][C:4]1[N:3]=[C:2]([NH:13][CH2:12][CH:9]2[CH2:11][CH2:10]2)[CH:7]=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 122742,6-DibromopyridineHCID 75646Cyclopropanemethanamine

Product 1

HCID 184089666-Bromo-N-(cyclopropylmethyl)pyridin-2-amineYield 82.4%

Reagents, catalysts & solvents 1

HCID 81531DiisopropylethylamineSolvent

Procedure

A solution of 2,6-dibromopyridine (33.0 g, 139 mmol) and cyclopropanemethylamine (10.8 g, 153 mmol) in DIPEA (27 mL) was heated at reflux for 24 h in a sealed pressure tube. The reaction mixture was cooled, concentrated in vacuo, and the residue was partitioned between EtOAc (250 mL) and saturated aqueous NaHCO3 (200 mL). The organic layer was washed with water (200 mL) followed by brine (200 mL) and dried (Na2SO4). The organic layer was filtered, concentrated in vacuo, and purified by flash chromatography (silica, 10% EtOAc/hexanes) affording 26 g of amine 2-1 as a white solid in 82% yield.

Workup

  1. temperatureat reflux for 24 h in a sealed pressure tube
  2. temperatureThe reaction mixture was cooled
  3. concentrationconcentrated in vacuo
  4. customthe residue was partitioned between EtOAc (250 mL) and saturated aqueous NaHCO3 (200 mL)
  5. washThe organic layer was washed with water (200 mL)
  6. dry with materialdried (Na2SO4)
  7. filtrationThe organic layer was filtered
  8. concentrationconcentrated in vacuo
  9. custompurified by flash chromatography (silica, 10% EtOAc/hexanes)

Sources & evidence

ORD record
ord-35f532bc335c464cb469f68c42f86963
Source dataset
uspto-grants-2002_10
Patent number
US06472403B2

Reaction notes

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