6-Methoxy-2-pyridinecarbonitrile → 1-(6-Methoxypyridin-2-YL)cyclopropan-1-amine

HRID 1040425Notes

Reaction equation

HRID 1040425 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[C:7]([C:9]#[N:10])[CH:6]=[CH:5][CH:4]=1.[CH3:11][CH2:12][Mg+].[Br-]>C1COCC1.O.CC(O[Ti](OC(C)C)(OC(C)C)OC(C)C)C>[CH3:1][O:2][C:3]1[N:8]=[C:7]([C:9]2([NH2:10])[CH2:12][CH2:11]2)[CH:6]=[CH:5][CH:4]=1

Participants

6

Reactant 2

HCID 130236446-Methoxy-2-pyridinecarbonitrileHCID 178461630HCID 178461630, compound

Product 1

HCID 584310411-(6-Methoxypyridin-2-YL)cyclopropan-1-amineYield 22%

Reagents, catalysts & solvents 3

HCID 178460666HCID 178460666, compoundCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 6-methoxy-pyridine-2-carbonitrile (1.50 g, 11.2 mmol) in THF (75 mL) at room temperature was added Ti(OiPr)4 (7.21 mL, 24.6 mmol). EtMgBr (14.9 mL, 44.7 mmol) was added dropwise. and the clear brown solution became heterogeneous. The reaction mixture was stirred for 1 h at room temperature. The reaction was diluted with water (10 mL), extracted with EtOAc (3×25 mL) and dried with MgSO4. After filtration, the solvent was removed in vacuo. The residue was purified by reverse phase HPLC to afford 380 mg (22%) of 1-(6-methoxy-pyridin-2-yl)-cyclopropylamine, m/z 166.3 [M+1]+.

Workup

  1. extractionextracted with EtOAc (3×25 mL)
  2. dry with materialdried with MgSO4
  3. filtrationAfter filtration
  4. customthe solvent was removed in vacuo
  5. customThe residue was purified by reverse phase HPLC

Sources & evidence

ORD record
ord-1950563d887f4ddea8e40216adfeccc5
Source dataset
uspto-grants-2013_10
Patent number
US08552205B2

Reaction notes

Loading…