反应 #2328995

ord-5861c2ece938468eb8787eb0c78469d6

反应方程式

COc1ccc2nc(Br)oc2c1
2-Bromo-6-methoxy-1,3-benzoxazole
CC1(C)OB(c2ccc(N)nc2)OC1(C)C
2-amino-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-pyridine
O=C([O-])[O-].[K+].[K+]
K2CO3
COc1ccc2nc(-c3ccc(N)nc3)oc2c1
title compound
收率 32.1%
COc1ccc2nc(-c3ccc(N)nc3)oc2c1
5-(6-methoxy-1,3-benzoxazol-2-yl)pyridin-2-amine
收率 32.1%

溶剂

反应条件

温度
80°CELSIUS
详细条件
See reaction.notes.procedure_details.

后处理

  1. 1
    其他The solvents were evaporated under reduced pressure
  2. 2
    其他followed by purification

实验过程

2-Bromo-6-methoxy-1,3-benzoxazole (0.877 mmol), 2-amino-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-pyridine (1.3 mmol), K2CO3 2M aq. (3.5 mmol) and Pd(dppf)Cl2 (0.022 mmol) were mixed in DMF (5 ml) and stirred at 80° C. for 2 h. The solvents were evaporated under reduced pressure and the crude product was subjected to flash column chromatography followed by purification using reverse phase HPLC to afford the title compound as a white solid (68 mg). 1H NMR δ ppm 8.67 (br. s, 1H) 8.12-7.91 (m, 1H) 7.69-7.51 (m, 1H) 7.34 (br. s, 1H) 6.89-7.00 (m, 1H) 6.75 (br. s, 2H) 6.43-6.65 (m, 1H) 3.84 (s, 3H); MS m/z 242 (M+H).

来源

DOI: 10.6084/m9.figshare.5104873.v1专利: US07670591B2uspto-grants-2010_03