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

HRID 541867Notes

Reaction equation

HRID 541867 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].CO>[NH2:1][C:2]1[CH:3]=[C:4]([CH2:8][CH2:9][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 57961822tert-Butyl {5-[2-(3-aminophenyl)ethyl]pyridin-3-yl}carbamateYield 99.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Into the reaction flask was added tert-butyl {5-[(3-aminophenyl)ethynyl]pyridin-3-yl}carbamate (0.50 g, 1.6 mmol), 50 mL of methanol and 10% palladium on carbon (100 mg, 0.094 mmol). The mixture was hydrogenated at 50 psi for 3 h. The reaction mixture was filtered to remove the catalyst and then concentrated under vacuum to give the desired product as an off-white powder (0.50 g, 99%). LCMS for C18H24N3O2 (M+H)+: m/z=314.1.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customto remove the catalyst
  3. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-24cdf051e80741f7a4e2cb9b640d63a3
Source dataset
uspto-grants-2014_10
Patent number
US08871753B2

Reaction notes

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