HCID 57961596, compound → tert-Butyl {2-[(Z)-2-(3-aminophenyl)vinyl]pyridin-4-yl}carbamate

HRID 541846Notes

Reaction equation

HRID 541846 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:8]#[C:9][C:10]2[CH:15]=[C:14]([NH:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])[CH:13]=[CH:12][N:11]=2)[CH:5]=[CH:6][CH:7]=1>CO.[Pd]>[NH2:1][C:2]1[CH:3]=[C:4](/[CH:8]=[CH:9]\[C:10]2[CH:15]=[C:14]([NH:16][C:17](=[O:23])[O:18][C:19]([CH3:21])([CH3:20])[CH3:22])[CH:13]=[CH:12][N:11]=2)[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 57961596HCID 57961596, compound

Product 1

HCID 57962525tert-Butyl {2-[(Z)-2-(3-aminophenyl)vinyl]pyridin-4-yl}carbamateYield 37%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a mixture of tert-butyl {2-[(3-aminophenyl)ethynyl]pyridin-4-yl}carbamate (430 mg, 1.4 mmol) in methanol (15 mL) was added 10% palladium on carbon (150 mg, 0.14 mmol) and hydrogenated at 60 psi for 20 hours. After filtration and concentration, the crude residue was purified by silica gel column chromatography to give the desired product (160 mg, 37%). LCMS for C18H22N3O2 (M+H)+: m/z=312.1

Workup

  1. filtrationAfter filtration and concentration
  2. customthe crude residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-a9056c0615064dab80ce34d6337b3c88
Source dataset
uspto-grants-2014_10
Patent number
US08871753B2

Reaction notes

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