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

HRID 541573Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 541573
[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]

Komponenten

5

Edukt 1

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

Produkt 1

HCID 89143988Tert-butyl{3-[2-(5-amino-2-methoxyphenyl)ethyl]phenyl}carbamateAusbeute 94,5 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23938PalladiumKatalysatorHCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  1. filtrationfiltered through celite
  2. customEvaporation of the filtrate

Quellen und Nachweise

ORD-Eintrag
ord-5dbfecb00ffa4509bb83608641408a9d
Quelldatensatz
uspto-grants-2014_10
Patentnummer
US08871753B2

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