تفاعل #10513

معادلة التفاعل

Na2CO3

5-bromo-2-[2-(2-methyl-pyrrolidin-1-yl)-ethyl]-1H-benzoimidazole

4-cyanophenylboronic acid

→

title compound

المردود 40.4%

4-{2-[2-(2-(R)-Methyl-pyrrolidin-1-yl)-ethyl]-1H-benzoimidazol-5-yl}-benzonitrile

المردود 40.4%

المذيبات

1,2-dimethoxyethane

H2O

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةthe reaction mixture was cooled
2. 2
   استخلاصextracted with ethyl acetate
3. 3
   غسيلThe organic layer was then washed with H2O
4. 4
   workup.DISTILLATIONdistilled to dryness
5. 5
   أخرىThe crude product was purified by column chromatography

الإجراء التجريبي

Nitrogen (N2) gas was bubbled through a solution of 5-bromo-2-[2-(2-methyl-pyrrolidin-1-yl)-ethyl]-1H-benzoimidazole (0.19 g, 0.6 mmol) and 4-cyanophenylboronic acid (0.13 g, 0.9 mmol) in 1,2-dimethoxyethane (4 mL) and H2O (2 mL). To the mixture was added 2M Na2CO3 (1.2 mL, 2.4 mmol) and Pd(dppf)2Cl2:CH2Cl2 (1:1), and this mixture heated to 80° C. After approximately 24 h, the reaction mixture was cooled and extracted with ethyl acetate. The organic layer was then washed with H2O and distilled to dryness. The crude product was purified by column chromatography to afford the title compound (0.08 g). 1H NMR (400 MHz, CDCl3) δ 1.18 (d, 3H), 1.52–1.62 (m, 1H), 1.77–1.95 (m, 2H), 2.03–2.12 (m, 1H), 2.30 (q, 1H), 2.47–2.56 (m, 1H), 2.57–2.62 (m, 1H), 3.15–3.20 (m, 2H), 3.21–3.35 (m, 2H), 7.43 (dd, J=1.7 & 8.3, 1H), 7.62 (d, 1H), 7.68–7.73 (m, 4H), 7.76 (s, 1H); 13C NMR (400 MHz, CDCl3) δ 19.5, 22.2, 27.4, 33.2, 51.5, 53.3, 60.5, 109.9, 118.9, 121.2, 127.5, 132.2, 133.0, 146.1, 156.1 (2 peaks overlapping and some 13C peaks were not readily identified due to exchange broadening). APP-IMS: (M+1)+ at 331 m/z.

المصدر