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Pd(0)-MEDIATED [11C]CARBONYLATION OF BORONIC ACID ESTERS WITH [11C]CARBON MONOXIDE
https://repo.qst.go.jp/records/65821
https://repo.qst.go.jp/records/65821582b3cc6-3112-488d-abac-9ce8f0037c7c
| Item type | 会議発表用資料 / Presentation(1) | |||||
|---|---|---|---|---|---|---|
| 公開日 | 2015-11-25 | |||||
| タイトル | ||||||
| タイトル | Pd(0)-MEDIATED [11C]CARBONYLATION OF BORONIC ACID ESTERS WITH [11C]CARBON MONOXIDE | |||||
| 言語 | ||||||
| 言語 | eng | |||||
| 資源タイプ | ||||||
| 資源タイプ識別子 | http://purl.org/coar/resource_type/c_c94f | |||||
| 資源タイプ | conference object | |||||
| アクセス権 | ||||||
| アクセス権 | metadata only access | |||||
| アクセス権URI | http://purl.org/coar/access_right/c_14cb | |||||
| 著者 |
Ishii, Hideki
× Ishii, Hideki× Minegishi, Katsuyuki× Nagatsu, Koutarou× Zhang, Ming-Rong× 石井 英樹× 峯岸 克行× 永津 弘太郎× 張 明栄 |
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| 抄録 | ||||||
| 内容記述タイプ | Abstract | |||||
| 内容記述 | Objectives: Introduction of carbonyl group into an aryl or heteroaryl groups is useful method for the construction of valuable pharmacologically active compounds. However typical carbonylation methods using [11C]O generally requires high pressure and high temperature conditions. Therefore, the development of amenable method for the [11C]carbonylation reaction is needed. Here we present the Pd(0)-mediated mild [11C]carbonylation reaction using [11C]O and boronic acid esters under atmospheric pressure.1 ,2 \nResults and discussion: The carbonylation reaction was carried out using [11C]O in the presence of aryl and heteroaryl boronic acid esters, paradium(II) acetate (Pd(OAc2)), p-benzoquinone (PBQ) and triphenylphosphine (PPh3) in MeOH or DMF-MeOH (v/v =1:1). The reaction mixture was heated at 65 °C for 5 min under atmospheric pressure to give corresponding [carbonyl-11C]esters. Some of these [carbonyl-11C]esters were converted to corresponding [carbonyl-11C]amides by treating with 25% ammonia solution at 65 °C for 5 - 10 min. Using this methods, we have been succeeded the synthesis of various aryl/heteroaryl [carbonyl-11C]esters with decay-corrected radiochemical yield (RCY) in the range of 6-80%. The efficiency of the amidation was deeply affected by the structure of the substrate. Although [carbonyl-11C]salicylamide, nicotinamide, 3-quinolineamide, 4-isoquinolineamide and 4-hydroxybenzamide were obtained in good RCY from corresponding [carbonyl-11C]esters, the production of 4-benzyloxy[carbonyl-11C]benzamide was failed. \nConclusions: Pd(0)-mediated [11C]carbonylation with aryl/heteroarylboronic acid pinacol esters and [11C]O have been carried out successfully in MeOH or DMF-MeOH (v/v =1:1) under atmospheric pressure at 65 °C for 5 min and gave the corresponding [carbonyl-11C]esters in the range of 6-80% RCY. Some of these [carbonyl-11C]esters were converted to the corresponding [carbonyl-11C]amides by treating with 25% ammonia solution. |
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| 会議概要（会議名, 開催地, 会期, 主催者等） | ||||||
| 内容記述タイプ | Other | |||||
| 内容記述 | Ninth Japan-China Joint Seminar on Radiopharmaceutical Chemistry | |||||
| 発表年月日 | ||||||
| 日付 | 2015-11-09 | |||||
| 日付タイプ | Issued | |||||
