Réaction #2146724

Équation de réaction

6a

Di-tert-butyl naphthalene-2,6-diylbis(methylene)bis(4,6-dimethylpyridin-2-ylcarbamate)

trifluoroacetic acid

→

3a

Rendement 90.0%

N,N′-(Naphthalene-2,6-diylbis(methylene))bis(4,6-dimethylpyridin-2-amine)

Rendement 90.0%

Solvants

CH2Cl2

Conditions de réaction

Traitement

1. 1
   Concentrationthen was concentrated
2. 2
   AutreThe crude product was purified by flash column chromatography (2-5% MeOH in CH2Cl2)

Mode opératoire

To a solution of 6a (590 mg, 1.0 mmol) in CH2Cl2 (8 mL) was added trifluoroacetic acid (TFA, 8 mL) The reaction mixture was allowed to stir at room temperature for 8 h then was concentrated. The crude product was purified by flash column chromatography (2-5% MeOH in CH2Cl2) to yield 3a (355 mg, 90%) as a white solid: 1H NMR (500 MHz, CD3OD/CDCl3) δ 2.28 (s, 6H), 2.48 (s, 6H), 4.60 (s, 4H), 6.46 (s, 4H), 7.45-7.47 (d, J=8.5, 2H), 7.78 (s, 2H), 7.84-7.86 (d, J=8.5, 2H); 13C NMR (125 MHz, CD3OD/CDCl3) δ 18.6, 22.0, 45.9, 106.8, 114.5, 125.6, 129.0, 133.1, 134.3, 147.6, 153.8, 158.0; ESI (M+H+) calcd for C26H29N4 397.23922, found 397.23999.

Source