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

HRID 541733Notes

Reaction equation

HRID 541733 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]=[CH:14][CH:15]=2)[CH:5]=[CH:6][CH:7]=1>CO.[Pd]>[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]=[CH:14][CH:15]=2)[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 57961975tert-Butyl {3-[(3-aminophenyl)ethynyl]phenyl}carbamate

Product 1

HCID 57962516tert-Butyl {3-[2-(3-aminophenyl)ethyl]phenyl}carbamateYield 85%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of tert-butyl {3-[(3-aminophenyl)ethynyl]phenyl}carbamate (0.5 g, 2.0 mmol) in methanol (10 mL) was added 10% palladium on carbon (0.50 g, 0.43 mmol) and the mixture was stirred under an atmosphere of hydrogen for 24 h. The reaction mixture was filtered through a pad of celite, rinsed with methanol and dichloromethane. The solvents were evaporated to give a crude oil. This material was purified by flash column chromatography to yield the desired product (430 mg, 85%). LCMS for C19H25N2O2(M+H)+: m/z=313.2.

Workup

  1. filtrationThe reaction mixture was filtered through a pad of celite
  2. washrinsed with methanol and dichloromethane
  3. customThe solvents were evaporated
  4. customto give a crude oil
  5. customThis material was purified by flash column chromatography

Sources & evidence

ORD record
ord-b8ea3b7391074aa5bd9763c8313e542f
Source dataset
uspto-grants-2014_10
Patent number
US08871753B2

Reaction notes

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