Water → 3-(Aminomethyl)-5-bromopyridine

HRID 2060078Notes

Reaction equation

HRID 2060078 reaction equation
[N:1]([CH2:4][C:5]1[CH:6]=[N:7][CH:8]=[C:9]([Br:11])[CH:10]=1)=[N+]=[N-].O.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>O1CCOCC1>[Br:11][C:9]1[CH:10]=[C:5]([CH2:4][NH2:1])[CH:6]=[N:7][CH:8]=1

Participants

5

Reactant 3

HCID 962WaterHCID 11776TriphenylphosphineHCID 576405383-(Azidomethyl)-5-bromopyridine

Product 1

HCID 229922643-(Aminomethyl)-5-bromopyridine

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of 3-azidomethyl-5-bromo-pyridine 250 (1.49 g, 7.00 mmol, 1.00 equiv) in 1,4-dioxane (12 mL) was added water (1 mL) and triphenylphosphine resin (2.08 g, 3 mol/g, 200-400 mesh, 1.2 equiv). The suspension was stirred overnight. Filtration and concentration afforded C-(5-bromo-pyridin-3-yl)-methylamine 251.

Workup

  1. filtrationFiltration and concentration

Sources & evidence

ORD record
ord-c55af4320ab04c0687036b976acfaa53
Source dataset
uspto-grants-2012_10
Patent number
US08278337B2

Reaction notes

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