tert-Butyl {5-[(3-aminophenyl)ethynyl]pyridin-3-yl}carbamate → tert-Butyl {5-[(Z)-2-(3-aminophenyl)vinyl]pyridin-3-yl}carbamate

HRID 541870Notes

Reaction equation

HRID 541870 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:8]#[C:9][C:10]2[CH:11]=[C:12]([NH:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])[CH:13]=[N:14][CH:15]=2)[CH:5]=[CH:6][CH:7]=1>[Pd].CC([O-])=O.CC([O-])=O.[Pb+2].CO>[NH2:1][C:2]1[CH:3]=[C:4](/[CH:8]=[CH:9]\[C:10]2[CH:11]=[C:12]([NH:16][C:17](=[O:23])[O:18][C:19]([CH3:21])([CH3:20])[CH3:22])[CH:13]=[N:14][CH:15]=2)[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 57961935tert-Butyl {5-[(3-aminophenyl)ethynyl]pyridin-3-yl}carbamate

Product 1

HCID 57962438tert-Butyl {5-[(Z)-2-(3-aminophenyl)vinyl]pyridin-3-yl}carbamateYield 43.6%

Reagents, catalysts & solvents 2

HCID 131709914Lindlars catalystCatalystHCID 887MethanolSolvent

Procedure

Into a reaction flask were added tert-butyl {5-[(3-aminophenyl)ethynyl]pyridin-3-yl}carbamate (0.45 g, 1.4 mmol) (prepared in Example C19, step A), methanol (15 mL) and 100 mg of Lindlar's catalyst. The reaction mixture was hydrogenated at 35 psi for 2 h. After removal of the solvent, the crude was purified by silica gel column chromatography to give the desired product as a white powder (0.19 g, 42%). LCMS for C18H22N3O2 (M+H)+: m/z=312.0.

Workup

  1. customAfter removal of the solvent
  2. customthe crude was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-7c5fa8cfeeb8492b9061d643625a861c
Source dataset
uspto-grants-2014_10
Patent number
US08871753B2

Reaction notes

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