Réaction #1783669

Équation de réaction

3-t-butyl-1-[4-(chloromethyl)naphthalen-2-yl]-1H-pyrazol-5-amine

NaN3

→

1-[4-(azidomethyl)naphthalen-2-yl]-3-t-butyl-1H-pyrazol-5-amine

Rendement 88.0%

Solvants

DMF

Conditions de réaction

Traitement

1. 1
   Extractionextracted with EtOAc (3×100 mL)
2. 2
   LavageThe combined organic extracts were washed with brine
3. 3
   Séchagedried (Na2SO4)
4. 4
   Filtrationfiltered
5. 5
   Concentrationconcentrated
6. 6
   Autrepurified via column chromatography

Mode opératoire

To a solution of 3-t-butyl-1-[4-(chloromethyl)naphthalen-2-yl]-1H-pyrazol-5-amine (1.5 g, 4.8 mmol) in DMF (8 mL) was added NaN3 (325 mg, 5.0 mmol). The mixture was stirred at RT overnight, then poured into ice-H2O and extracted with EtOAc (3×100 mL). The combined organic extracts were washed with brine, dried (Na2SO4), filtered, concentrated and purified via column chromatography to afford 1-[4-(azidomethyl)naphthalen-2-yl]-3-t-butyl-1H-pyrazol-5-amine (1.35 g, 88% yield). 1H NMR (300 MHz, DMSO-d6): δ 8.06 (m, 2H), 8.04 (m, 1H), 7.85 (s, 1H), 7.54-7.57 (m, 2H), 5.41 (s, 1H), 5.35 (brs, 2H), 4.96 (s, 2H), 1.21 (s, 9H); MS (ESI) m/z: 321 (M+H+).

Source