Microwave-assisted synthesis of 3-aminobenzo[b]thiophene scaffolds for the preparation of kinase inhibitors.
Microwave-assisted synthesis of 3-aminobenzo[b]thiophene scaffolds for the preparation of kinase inhibitors.
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DOI：
10.1039/c5ob00819k
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发表时间：
2015-06
影响因子：
3.2
通讯作者：
M. Bagley;J. Dwyer;M. D. Molina;A. W. Rand;H. Rand;N. Tomkinson
中科院分区：
文献类型：
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作者：
M. Bagley;J. Dwyer;M. D. Molina;A. W. Rand;H. Rand;N. Tomkinson
微波辐射2-卤代苯甲腈和巯基乙酸甲酯在三乙胺存在下的DMSO中在130 °C提供快速获得3-氨基苯并[B]噻吩，产率为58-96%。这种转化已应用于合成LIMK 1抑制剂的噻吩并[2，3-B]吡啶核心基序、MK 2抑制剂的苯并[4，5]噻吩并[3，2-e][1，4]二氮杂卓-5（2 H）-酮骨架和PIM激酶的苯并[4，5]噻吩并[3，2-d]嘧啶-4-酮抑制剂。
Microwave irradiation of 2-halobenzonitriles and methyl thioglycolate in the presence of triethylamine in DMSO at 130 °C provides rapid access to 3-aminobenzo[b]thiophenes in 58-96% yield. This transformation has been applied in the synthesis of the thieno[2,3-b]pyridine core motif of LIMK1 inhibitors, the benzo[4,5]thieno[3,2-e][1,4]diazepin-5(2H)-one scaffold of MK2 inhibitors and a benzo[4,5]thieno[3,2-d]pyrimidin-4-one inhibitor of the PIM kinases.