Reaktion #314105

Reaktionsgleichung

3-(3,4-dimethyl-benzoyl)-1-prop-2-ynyl-1H-quinolin-4-one

3-(3,4-Dimethyl-benzoyl)-1-prop-2-ynyl-1H-quinolin-4-one

tert-butyl-carbamic acid azidomethyl ester

sodium hydroxide

→

pale yellow product

Ausbeute 54.6%

3-(3,4-Dimethyl-benzoyl)-1-(1H-[1,2,3]triazol-4-ylmethyl)-1H-quinolin-4-one

Ausbeute 54.6%

Lösungsmittel

tert-butanol

water

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   FiltrationThe mixture was filtered
2. 2
   Sonstigepurified
3. 3
   Sonstigein 50 min
4. 4
   workup.ADDITIONLyophilization of the HPLC fractions containing
5. 5
   Sonstigepurified 4d

Vorschrift

29 mg (0.092 mmol) of 3-(3,4-dimethyl-benzoyl)-1-prop-2-ynyl-1H-quinolin-4-one 4c (prepared as described by Paine, J. B.; J. Het. Chem. 1987, 351), 19 mg (0.11 mmol) of tert-butyl-carbamic acid azidomethyl ester, 5.0 mg (0.078 mmol) of copper powder, and 2.0 mg (0.008 mmol) of copper(II) sulfate pentahydrate were combined in a mixture of 0.5 mL tert-butanol and 0.2 mL water and stirred at 80° C. for 4 h. Then 70 mg (1.75 mmol) of sodium hydroxide in 1 mL water was added to that mixture and the resultant mixture was stirred at 80° C. for another hour. The mixture was filtered and purified using reverse phase HPLC (mobile phase with a gradient 15-80% acetonitrile in 50 min). Lyophilization of the HPLC fractions containing purified 4d provided 18 mg of a pale yellow product as the trifluoroacetate salt: LC-MSD, m/z for C21H18N4O2, [M+H]+=359.5, HPLC retention time: 1.5 min; 1H NMR (400 MHz, CDCl3): δ 2.25 (s, 3H), 2.3 (s, 3H), 6.7 (s, 2H), 7.1-7.2 (m, 1H), 7.4-7.45 (m, 1H), 7.45-7.5 (m, 2H), 7.75-7.85 (m, 3H), 8.4-8.5 (m, 1H), 8.65 (s, 1H).

Quelle