反応 #10513

反応方程式

Na2CO3

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

4-cyanophenylboronic acid

→

title compound

収率 40.4%

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

収率 40.4%

溶媒

1,2-dimethoxyethane

H2O

反応条件

後処理

1. 1
   温度the reaction mixture was cooled
2. 2
   抽出extracted with ethyl acetate
3. 3
   洗浄The organic layer was then washed with H2O
4. 4
   workup.DISTILLATIONdistilled to dryness
5. 5
   その他The crude product was purified by column chromatography

実験手順

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.

出典