Tert-butyl{3-[(2-methoxy-5-nitrophenyl)ethynyl]phenyl}carbamate → Tert-butyl{3-[2-(5-amino-2-methoxyphenyl)ethyl]phenyl}carbamate

HRID 541573Notes

Reaction equation

HRID 541573 reaction equation
[C:1]([O:5][C:6](=[O:27])[NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([C:14]#[C:15][C:16]2[CH:21]=[C:20]([N+:22]([O-])=O)[CH:19]=[CH:18][C:17]=2[O:25][CH3:26])[CH:9]=1)([CH3:4])([CH3:3])[CH3:2]>[Pd].CN(C)C=O.C(OCC)(=O)C>[C:1]([O:5][C:6](=[O:27])[NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([CH2:14][CH2:15][C:16]2[CH:21]=[C:20]([NH2:22])[CH:19]=[CH:18][C:17]=2[O:25][CH3:26])[CH:9]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 1

HCID 57961666Tert-butyl{3-[(2-methoxy-5-nitrophenyl)ethynyl]phenyl}carbamate

Product 1

HCID 89143988Tert-butyl{3-[2-(5-amino-2-methoxyphenyl)ethyl]phenyl}carbamateYield 94.5%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

tert-Butyl{3-[(2-methoxy-5-nitrophenyl)ethynyl]phenyl}carbamate (63 mg, 0.17 mmol) and 10% palladium on carbon (122 mg, 0.10 mmol) were stirred in N,N-dimethylformamide (3.0 mL) under an atmosphere of hydrogen for 16 hours. The mixture was diluted with ethyl acetate (9.0 mL) and filtered through celite. Evaporation of the filtrate gave the desired compound (55 mg, 94%). LCMS for C20H27N2O3 (M+H)+: m/z=343.2.

Workup

  1. filtrationfiltered through celite
  2. customEvaporation of the filtrate

Sources & evidence

ORD record
ord-5dbfecb00ffa4509bb83608641408a9d
Source dataset
uspto-grants-2014_10
Patent number
US08871753B2

Reaction notes

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