2-(Pyridin-3-yl)ethan-1-amine → tert-Butyl 3-{[2-(pyridin-3-yl)ethyl]amino}benzoate

HRID 750997Notes

Reaction equation

HRID 750997 reaction equation
[NH2:1][CH2:2][CH2:3][C:4]1[CH:5]=[N:6][CH:7]=[CH:8][CH:9]=1.I[C:11]1[CH:12]=[C:13]([CH:21]=[CH:22][CH:23]=1)[C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15].CC(C)([O-])C.[Na+].F[B-](F)(F)F.C([PH+](C(C)(C)C)C(C)(C)C)(C)(C)C>C1(C)C=CC=CC=1>[N:6]1[CH:7]=[CH:8][CH:9]=[C:4]([CH2:3][CH2:2][NH:1][C:11]2[CH:12]=[C:13]([CH:21]=[CH:22][CH:23]=2)[C:14]([O:16][C:17]([CH3:19])([CH3:20])[CH3:18])=[O:15])[CH:5]=1

Participants

6

Reactant 4

HCID 8540512-(Pyridin-3-yl)ethan-1-amineHCID 2734635Tri-tert-butylphosphine tetrafluoroborateHCID 18386959tert-Butyl 3-iodobenzoateHCID 23676156Sodium t-butoxide

Product 1

HCID 68952622tert-Butyl 3-{[2-(pyridin-3-yl)ethyl]amino}benzoateYield 17.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a mixture of 244 mg of 3-(2-aminoethyl)pyridine (2.0 mmol) and 604 mg of t-butyl 3-iodobenzoate (2.0 mmol) in 10 mL of toluene was added 250 mg of sodium t-butoxide (2.5 mmol), 30 mg of tri-t-butylphosphonium tetrafluoroborate (0.1 mmol) and 50 mg of tris(dibenzylidineacetone)dipalladium(0) (0.055 mmol). The mixture was stirred for 16 h and filtered through celite. The celite was washed with 3×5 mL of toluene and the filtrate was concentrated in vacuo. The residue was purified by column chromatography using 35%-45% EtOAc in hexanes as eluant to give 103 mg of t-butyl N-(2-(3-pyridyl)ethyl)-3-aminobenzoate as a bright yellow oil (17% yield).

Workup

  1. filtrationfiltered through celite
  2. washThe celite was washed with 3×5 mL of toluene
  3. concentrationthe filtrate was concentrated in vacuo
  4. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-d173864558db44b58db5320d23fd7d02
Source dataset
uspto-grants-2008_07
Patent number
US07405230B2

Reaction notes

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