Reaktion #40530

Reaktionsgleichung

NaHCO3

pyridine-3-boronic acid 1,3-propanediol cyclic ester

(2-amino-5-bromo-3-nitro-phenyl)-cyclohexyl-methanone

→

title compound

Ausbeute 89.0%

(2-Amino-3-nitro-5-pyridin-3-yl-phenyl)-cyclohexyl-methanone

Ausbeute 89.0%

Lösungsmittel

EtOAc

DME

Reaktionsbedingungen

Aufarbeitung

1. 1
   Waschenwashed with water (50 mL), brine (50 mL)
2. 2
   Trocknendried (MgSO4)
3. 3
   Filtrationfiltered
4. 4
   Einengenthe filtrate concentrated in vacuo
5. 5
   SonstigeThe resulting residue was purified by flash chromatography (SiO2, hexanes to 3:1 hexanes:EtOAc)

Vorschrift

To a solution of (2-amino-5-bromo-3-nitro-phenyl)-cyclohexyl-methanone (600 mg, 1.83 mmol) in DME (25 mL) was added, successively, pyridine-3-boronic acid 1,3-propanediol cyclic ester (388 mg, 2.38 mmol), (tetrakistriphenylphosphine) palladium(0) (212 mg, 0.18 mmol), and 1N NaHCO3 (3.7 mL, 3.7 mmol). The resulting mixture was stared at 90° C. for 90 minutes then cooled to room temperature. The reaction mixture was diluted with EtOAc (100 mL), washed with water (50 mL), brine (50 mL), dried (MgSO4), filtered and the filtrate concentrated in vacuo. The resulting residue was purified by flash chromatography (SiO2, hexanes to 3:1 hexanes:EtOAc) to afford 527 mg (89%) of the title compound as a pale orange solid: 1H NMR (CDCl3, 500 MHz) δ 8.92 (d, 1H), 8.69 (d, 1H), 8.66 (d, 1H), 8.31 (d, 1H), 8.20 (d, 1H), 7.71 (dd, 1H), 3.36 (m, 1H), 1.88 (m, 3H), 1.77 (m, 1H), 1.40-1.61 (m, 3H), 1.24-1.32 (m, 2H), 0.89 (m, 1H).

Quelle