5-Iodopyridine-2-carbonitrile → 1-(5-Iodo-pyridin-2-yl)-cyclopropylamine

HRID 449162Notes

Reaction equation

HRID 449162 reaction equation
[I:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]#[N:9])=[N:6][CH:7]=1.[CH3:10][CH2:11][Mg+].[Br-]>C1COCC1.O.Cl.CC(C)[O-].[Ti+4].CC(C)[O-].CC(C)[O-].CC(C)[O-]>[I:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2([NH2:9])[CH2:11][CH2:10]2)=[N:6][CH:7]=1

Participants

7

Reactant 2

HCID 378183975-Iodopyridine-2-carbonitrileHCID 178461630HCID 178461630, compound

Product 1

HCID 584311461-(5-Iodo-pyridin-2-yl)-cyclopropylamineYield 20.4%

Reagents, catalysts & solvents 4

HCID 11026Titanium isopropoxideCatalystHCID 313Hydrochloric AcidSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-iodo-pyridine-2-carbonitrile (1.0 g, 8.1 mmol) in dry THF (50 mL) was added titanium(IV) isopropoxide (5.2 mL, 18 mmol). EtMgBr (3.0M in Et2O, 10 mL, 32 mmol) was then added dropwise. The reaction mixture was stirred for 23 h, then diluted with water (100 mL) and 1N HCl (5 mL), and stirred for 5 minutes. The mixture was filtered and the filtrate was concentrated in-vacuo to afford 430 mg of the title compound which was used without further purification.

Workup

  1. stirringstirred for 5 minutes
  2. filtrationThe mixture was filtered
  3. concentrationthe filtrate was concentrated in-vacuo

Sources & evidence

ORD record
ord-a65d37e571654f8a8fd575ef05d48337
Source dataset
uspto-grants-2013_07
Patent number
US08481750B2

Reaction notes

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