تفاعل #2055864

معادلة التفاعل

NaHCO3

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

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

→

title compound

المردود 89.0%

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

المردود 89.0%

المذيبات

EtOAc

DME

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةthen cooled to room temperature
2. 2
   غسيلwashed with water (50 mL), brine (50 mL)
3. 3
   تجفيفdried (MgSO4)
4. 4
   ترشيحfiltered
5. 5
   تركيزthe filtrate concentrated in vacuo
6. 6
   أخرىThe resulting residue was purified by flash chromatography (SiO2, hexanes to 3:1 hexanes:EtOAc)

الإجراء التجريبي

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 stirred 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).

المصدر