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【结 构 式】

【分子编号】69164

【品名】(2-pyridyl)zinc iodide

【CA登记号】 

【 分 子 式 】C5H4INZn

【 分 子 量 】270.388

【元素组成】C 22.21% H 1.49% I 46.93% N 5.18% Zn 24.18%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号:(III)

Sandmeyer reaction of 2-chloro-5-nitroaniline (I) with NaNO2 in the presence of KI gives 1-chloro-2-iodo-4-nitrobenzene (II), which is then coupled with (2-pyridyl)zinc iodide (III) by means of Pd(PPh3)4, tris(2-furyl)phosphine and CuI in THF/DMAc to provide the phenylpyridine derivative (IV). After nitro group reduction in compound (IV) using either Fe and AcOH at 80 °C or SnCl2 and HCl in EtOH , the resulting pyridylaniline (V) is finally acylated with either 2-chloro-4-(methylsulfonyl)benzoyl chloride (VI) in the presence of Et3N in CH2Cl2 or 2-chloro-4-(methylsulfonyl)benzoic acid (VII) by means of HATU and DIEA in DMF .

1 Robarge, K.D., Brunton, S.A., Castanedo, G.M. et al. GDC-0449 - A potent inhibitor of the hedgehog pathway. Bioorg Med Chem Lett 2009, 19(19): 5576-81.
2 Gunzner, J., Sutherlin, D., Stanley, M. et al. (Genentech, Inc.; Curis, Inc.). Pyridyl inhibitors of hedgehog signalling. EP 1789390, JP 2008511675, WO 2006028958.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(I) 43033 2-chloro-5-nitroaniline; 2-chloro-5-nitrophenylamine 6283-25-6 C6H5ClN2O2 详情 详情
(II) 69162 1-chloro-2-iodo-4-nitrobenzene;4-Chloro-3-iodonitrobenzene 74534-15-9 C6H3ClINO2 详情 详情
(III) 69164 (2-pyridyl)zinc iodide   C5H4INZn 详情 详情
(IV) 69163 2-(2-chloro-5-nitrophenyl)pyridine   C11H7ClN2O2 详情 详情
(V) 69165 4-chloro-3-(pyridin-2-yl)aniline   C11H9ClN2 详情 详情
(VI) 69166 2-chloro-4-(methylsulfonyl)benzoyl chloride;2-chloro-5-(methylsulfonyl)benzoyl chloride   C8H6Cl2O3S 详情 详情
(VII) 69167 2-chloro-4-(methylsulfonyl)benzoic acid;2-chloro-5-(methylsulfonyl)benzoic acid 89938-62-5 C8H7ClO4S 详情 详情
Extended Information