Reaktion #1136452

Reaktionsgleichung

3-((2-ethynylpyridin-4-yl)oxy)-2-methyl-6-nitropyridine

2,6-lutidine

azidomethyl pivalate

→

(4-(4-((2-methyl-6-nitropyridin-3-yl)oxy)pyridin-2-yl)-1H-1,2,3-triazol-1-yl)methyl pivalate

Ausbeute 84.0%

Lösungsmittel

tert-butanol

MeCN

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe mixture was partitioned between water (30 mL) and EtOAc (30 mL)
2. 2
   ExtraktionThe aqueous layer was extracted with EtOAc
3. 3
   Waschenthe combined organics were washed with brine
4. 4
   Trocknendried (Na2SO4)
5. 5
   Einengenconcentrated
6. 6
   SonstigeThe crude product was purified by silica gel chromatography (EtOAc/Hex)

Vorschrift

A solution of 3-((2-ethynylpyridin-4-yl)oxy)-2-methyl-6-nitropyridine (0.2 g, 0.78 mmol) and azidomethyl pivalate (0.209 g, 1.33 mmol; See: Syn Lett. 2005, (18), 2847-2850) were combined in tert-butanol (3 mL) and treated with copper(I) iodide (0.030 g, 0.157 mmol) followed by a solution of 2,6-lutidine (0.091 mL, 0.78 mmol) in MeCN (3 mL) and the resultant mixture was stirred at RT for 3 h. The mixture was partitioned between water (30 mL) and EtOAc (30 mL). The aqueous layer was extracted with EtOAc and the combined organics were washed with brine, dried (Na2SO4) and concentrated. The crude product was purified by silica gel chromatography (EtOAc/Hex) to afford (4-(4-((2-methyl-6-nitropyridin-3-yl)oxy)pyridin-2-yl)-1H-1,2,3-triazol-1-yl)methyl pivalate (0.27 g, 84%) as an orange foam. 1H NMR (400 MHz, DMSO-d6): δ 8.74 (s, 1H), 8.60 (d, J=5.7 Hz, 1H), 8.26 (d, J=8.7 Hz, 1H), 7.94 (d, J=8.7 Hz, 1H), 7.64 (d, J=2.4 Hz, 1H), 7.12 (dd, J=5.6, 2.5 Hz, 1H), 6.37 (s, 2H), 2.50 (s, 3H), 1.11 (s, 9H); MS (ESI) m/z: 413.2 (M+H+).

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