{"created":"2023-05-15T14:56:02.738766+00:00","id":76113,"links":{},"metadata":{"_buckets":{"deposit":"e6242d69-ee09-433b-9dcc-c1c5fce04318"},"_deposit":{"created_by":1,"id":"76113","owners":[1],"pid":{"revision_id":0,"type":"depid","value":"76113"},"status":"published"},"_oai":{"id":"oai:repo.qst.go.jp:00076113","sets":["10:28"]},"author_link":["765139","765143","765144","765140","765142","765141"],"item_10005_date_7":{"attribute_name":"発表年月日","attribute_value_mlt":[{"subitem_date_issued_datetime":"2019-05-28","subitem_date_issued_type":"Issued"}]},"item_10005_description_5":{"attribute_name":"抄録","attribute_value_mlt":[{"subitem_description":"Objectives\nThe introduction of nitrile group to the organic compounds is one of the most attractive way for the synthesis of drugs, agriculture, and functional materials. And its facile conversion to the other functional groups, such as carboxylic acid, amide, tetrazole, and so on, is also synthetically useful method too. Generally, the introduction of nitrile group is conducted with appropriate cyanide source and halogen, pseudo-halides, stannanes, and organoborons in the presence of transition metal. These methods are also applied for the introduction of [11C]CN , and we have used Rosenmund-von Braun reaction for this purepos, so far.[1] Here we report the CuI-mediated 11C-cyanation of (hetero)aromatic compounds.\n\nMethods\n[11C]CN was synthesized by reducing [11C]CO2 to [11C]methane with nickel under H2 atmosphere and then oxidizing it with Pt under NH3 atmosphere. The generated [11C]NH4CN was bubbled to reaction vessel containing CuI and (hetero)aromatic bromide at room temperature. The reaction mixture was heated at 180 °C for 5 min, then was purified by reverse phase HPLC to give corresponding [11C]CN labelled products in good  radiochemical yields.\n.\nResults\nCuI-mediated 11CN-labelling have been successfully applied to model heteroaromatic bromide, such as 3-bromopyridine and 3-bromoquinoline. Thus, we have applied this method for synthesis of [11C]perampanel which was obtained 30%, (decay corrected to the end of bombardment) with  >99% of radiochemical purities  and 84 GBq/μmol of molar activity at the end of synthesis.\n\nConclusions\nWe have successfully achieved CuI-mediated 11CN-labelling of (hetero)aromatic compounds. Further applications of this reaction are currently under investigation\n\nAcknowledgements\nThis work was supported by JSPS KAKENHI Grant Number 17K10383.\n\nReferences\n[1] Oi, N., Tokunaga, M., et al., J. Med. Chem. 2015, 58, 8444-8462.\n","subitem_description_type":"Abstract"}]},"item_10005_description_6":{"attribute_name":"会議概要（会議名, 開催地, 会期, 主催者等）","attribute_value_mlt":[{"subitem_description":"ISRS2019でのポスター発表","subitem_description_type":"Other"}]},"item_access_right":{"attribute_name":"アクセス権","attribute_value_mlt":[{"subitem_access_right":"metadata only access","subitem_access_right_uri":"http://purl.org/coar/access_right/c_14cb"}]},"item_creator":{"attribute_name":"著者","attribute_type":"creator","attribute_value_mlt":[{"creatorNames":[{"creatorName":"Ishii, Hideki"}],"nameIdentifiers":[{"nameIdentifier":"765139","nameIdentifierScheme":"WEKO"}]},{"creatorNames":[{"creatorName":"Okamura, Toshimitsu"}],"nameIdentifiers":[{"nameIdentifier":"765140","nameIdentifierScheme":"WEKO"}]},{"creatorNames":[{"creatorName":"Ming-Rong, Zhang"}],"nameIdentifiers":[{"nameIdentifier":"765141","nameIdentifierScheme":"WEKO"}]},{"creatorNames":[{"creatorName":"Ishii, Hideki","creatorNameLang":"en"}],"nameIdentifiers":[{"nameIdentifier":"765142","nameIdentifierScheme":"WEKO"}]},{"creatorNames":[{"creatorName":"Okamura, Toshimitsu","creatorNameLang":"en"}],"nameIdentifiers":[{"nameIdentifier":"765143","nameIdentifierScheme":"WEKO"}]},{"creatorNames":[{"creatorName":"Ming-Rong, Zhang","creatorNameLang":"en"}],"nameIdentifiers":[{"nameIdentifier":"765144","nameIdentifierScheme":"WEKO"}]}]},"item_language":{"attribute_name":"言語","attribute_value_mlt":[{"subitem_language":"eng"}]},"item_resource_type":{"attribute_name":"資源タイプ","attribute_value_mlt":[{"resourcetype":"conference object","resourceuri":"http://purl.org/coar/resource_type/c_c94f"}]},"item_title":"CuI-mediated 11C-cyanation of (hetero)aromatic bromide  and synthesis of [11C]perampanel","item_titles":{"attribute_name":"タイトル","attribute_value_mlt":[{"subitem_title":"CuI-mediated 11C-cyanation of (hetero)aromatic bromide  and synthesis of [11C]perampanel"}]},"item_type_id":"10005","owner":"1","path":["28"],"pubdate":{"attribute_name":"公開日","attribute_value":"2019-06-03"},"publish_date":"2019-06-03","publish_status":"0","recid":"76113","relation_version_is_last":true,"title":["CuI-mediated 11C-cyanation of (hetero)aromatic bromide  and synthesis of [11C]perampanel"],"weko_creator_id":"1","weko_shared_id":-1},"updated":"2023-05-16T00:36:59.018924+00:00"}