title: Microwave-assisted synthesis of 3-aminobenzo[b]thiophene scaffolds for the preparation of kinase inhibitors.
abstract: 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.
authors.affiliation: Department of Chemistry, School of Life Sciences, University of Sussex, Falmer, Brighton, East Sussex, BN1 9QJ, UK. m.c.bagley@sussex.ac.uk.
authors.forename: Mark C
authors.initials: MC
authors.lastname: Bagley
authors.forename: Jessica E
authors.initials: JE
authors.lastname: Dwyer
authors.forename: Maria D Beltran
authors.initials: MD
authors.lastname: Molina
authors.forename: Alexander W
authors.initials: AW
authors.lastname: Rand
authors.forename: Hayley L
authors.initials: HL
authors.lastname: Rand
authors.forename: Nicholas C O
authors.initials: NC
authors.lastname: Tomkinson
mesh_terms: D000586:Amination; D006801:Humans; D054461:Lim Kinases / Q000037:antagonists & inhibitors; D048370:MAP Kinase Kinase 2 / Q000037:antagonists & inhibitors; D008872:Microwaves; D047428:Protein Kinase Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry; D051573:Proto-Oncogene Proteins c-pim-1 / Q000037:antagonists & inhibitors; D013876:Thiophenes / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D047428:Protein Kinase Inhibitors; D013876:Thiophenes; C088015:benzothiophene; C515892:LIMK1 protein, human; D054461:Lim Kinases; D051573:Proto-Oncogene Proteins c-pim-1; C406031:proto-oncogene proteins pim; D048370:MAP Kinase Kinase 2