Reaktion #2147905

Reaktionsgleichung

azidomethyl pivalate

4-(2-ethynylpyridin-4-yloxy)-2-fluorobenzenamine

sodium ascorbate

→

(4-(4-(4-amino-3-fluorophenoxy)pyridin-2-yl)-1H-1,2,3-triazol-1-yl)methyl pivalate

Ausbeute 90.0%

Lösungsmittel

t-butanol

water

EtOAc

water

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigethe layers were separated
2. 2
   Extraktionthe aqueous layer was extracted with EtOAc (2×15 mL)
3. 3
   WaschenThe combined organics were washed with brine
4. 4
   Trocknendried (Na2SO4)
5. 5
   Einengenconcentrated

Vorschrift

To a suspension of azidomethyl pivalate (0.075 g, 0.477 mmol), 4-(2-ethynylpyridin-4-yloxy)-2-fluorobenzenamine from Example A21 (0.109 g, 0.477 mmol) in t-butanol (0.6 mL) and water (0.6 mL) was added sodium ascorbate (0.021 g, 0.095 mmol). Copper(II)sulfate in water (0.048 ml, 0.048 mmol) was added to the above suspension and the dark red mixture was stirred for 3 h at RT. It was diluted with water (30 mL) and EtOAc (20 mL), the layers were separated and the aqueous layer was extracted with EtOAc (2×15 mL). The combined organics were washed with brine, dried (Na2SO4) and concentrated to afford (4-(4-(4-amino-3-fluorophenoxy)pyridin-2-yl)-1H-1,2,3-triazol-1-yl)methyl pivalate as a red solid. (0.165 g, 90% yield). 1H NMR (400 MHz, DMSO-d6): δ 8.54 (s, 1H), 8.46 (brs, 1H), 7.60 (s, 1H), 6.98 (d, J=8.8 Hz, 1H), 6.94 (d, J=3.6 Hz, 1H), 6.83-6.81 (m, 2H), 6.42 (s, 2H), 4.78 (s, 2H), 1.17 (s, 9H); MS (ESI) m/z: 386.1 (M+H+).

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