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Synthesis of Thiophene-Based TAK-779 Analogues by C-H Arylation

Synthesis of Thiophene-Based TAK-779 Analogues by C-H Arylation

Anna Junker, Junichiro Yamaguchi, Kenichiro Itami, Bernhard Wünsch

J Org Chem. 2013 Jun 7;78(11):5579-86.

PMID: 23642160

Abstract:

A rapid synthesis of thiophene-based TAK-779 analogues 1 is reported using a late-stage diversification strategy. At the end of the synthesis, the key building block 2, which was prepared in six steps from thiophene, was arylated regioselectively at the α-position directly with iodoarenes. Since 2 offers several reactive positions, various established catalyst systems were tested. It was found that Crabtree catalyst (an Ir catalyst) converted efficiently and selectively the thiophene system 2 into 2-aryl-substituted compounds 9. The direct C-H arylation of 2 with electron-rich iodoarenes led to high yields, whereas electron-deficient iodoarenes required longer reaction times for complete conversion. A small set of diverse amides 1 was synthesized by hydrolysis of 9 and subsequent HATU coupling with primary amines 4.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP229005805	TAK-779		229005-80-5	Price

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