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METHOD FOR METHYLATING sp³ CARBON

Foreign code	F140007837
File No.	S2012-0926-C0
Posted date	Feb 14, 2014
Country	WIPO
International application number	2013JP069548
International publication number	WO 2014014067
Date of international filing	Jul 18, 2013
Date of international publication	Jan 23, 2014
Priority data	P2012-159725 (Jul 18, 2012) JP
Title	METHOD FOR METHYLATING sp³ CARBON
Abstract	[Problem] The present invention addresses the problem of providing a method for rapidly methylating sp³ carbon under conditions having a low [¹¹C]CH₃I concentration, which is applicable to the methylation of [¹¹C]. [Solution] The method for methylating sp³ carbon according to the present invention is characterized by cross-coupling a boronic acid ester compound in which a carbon atom at an allyl position or a benzyl position has been esterified with boronic acid and methyl iodide in an aprotic polar solvent such as DMF under such a condition that a palladium complex represented by general formula Pd[PR¹R²R³]₂ (wherein at least one of three substituents R¹, R² and R³ is an alkyl group) and a base are present. It is preferred that the aprotic polar solvent contains water. Examples of the compounds represented by general formula Pd[PR¹R²R³]₂ include Pd[P(tert-C₄H₉)₃]₂ and others.
Scope of claims	(In Japanese)[請求項1] 非プロトン性極性溶媒中において、アリル位又はベンジル位の炭素がボロン酸エステル化されたボロン酸エステル化合物とヨウ化メチルとを、一般式がPd[PR¹R²R³]₂で示されるパラジウム錯体（ただし、R¹、R²、R³の三置換基のうち少なくとも一つはアルキル基）及び塩基が存在する条件下でクロスカップリングさせることを特徴とするsp³炭素のメチル化法。 [請求項2] 前記非プロトン性極性溶媒はアミド系極性溶媒である請求項1に記載のsp³炭素のメチル化法。 [請求項3] 前記反応溶媒には水が含まれていることを特徴とする請求項1又は2に記載のsp³炭素のメチル化法。 [請求項4] 前記塩基はアルカリ金属の炭酸塩及び/又はアルカリ金属のフッ化物である請求項1乃至3のいずれか1項に記載のsp³炭素のメチル化法。 [請求項5] 前記パラジウム錯体はPd[P（tert-C₄H₉）₃]₂であることを特徴とする請求項1乃至4のいずれか1項に記載のsp³炭素のメチル化法。 [請求項6] 前記ボロン酸エステル化合物はベンジルボロン酸エステル及びその誘導体、並びに、シンナミルボロン酸エステル及びその誘導体、のいずれかであることを特徴とする請求項1乃至5のいずれか1項に記載のsp³炭素のメチル化法。 [請求項7] ボロン酸エステル化合物のモル数はヨウ化メチルのモル数の40倍以上とされていることを特徴とする請求項1乃至7のいずれか1項に記載のsp³炭素のメチル化法。
Applicant ※All designated countries except for US in the data before July 2012	RIKEN GIFU UNIVERSITY
Inventor	SUZUKI MASAAKI IJUIN RYOSUKE DOI HISASHI KOYAMA HIROKO
IPC(International Patent Classification)	C07C 1/32 starting from compounds containing hetero atoms other than, or in addition to, oxygen or halogen C07B 59/00 Introduction of isotopes of elements into organic compounds C07B 61/00 Other general methods C07C 15/073 Ethylbenzene
Specified countries	National States: AE AG AL AM AO AT AU AZ BA BB BG BH BN BR BW BY BZ CA CH CL CN CO CR CU CZ DE DK DM DO DZ EC EE EG ES FI GB GD GE GH GM GT HN HR HU ID IL IN IS JP KE KG KN KP KR KZ LA LC LK LR LS LT LU LY MA MD ME MG MK MN MW MX MY MZ NA NG NI NO NZ OM PA PE PG PH PL PT QA RO RS RU RW SC SD SE SG SK SL SM ST SV SY TH TJ TM TN TR TT TZ UA UG US UZ VC VN ZA ZM ZW ARIPO: BW GH GM KE LR LS MW MZ NA RW SD SL SZ TZ UG ZM ZW EAPO: AM AZ BY KG KZ RU TJ TM EPO: AL AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HR HU IE IS IT LT LU LV MC MK MT NL NO PL PT RO RS SE SI SK SM TR OAPI: BF BJ CF CG CI CM GA GN GQ GW KM ML MR NE SN TD TG

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Gifu University (In Japanese)産官学連携推進本部　知的財産部門
URL: http://www.sangaku.gifu-u.ac.jp/
E-mail:
Address: 1-1, Yanagito, Gifu-shi, Gifu-ken , 501-1193
Fax: 058-293-3346

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Contact Information for " METHOD FOR METHYLATING sp³ CARBON "

Gifu University (In Japanese)産官学連携推進本部　知的財産部門
URL: http://www.sangaku.gifu-u.ac.jp/
E-mail:
Address: 1-1, Yanagito, Gifu-shi, Gifu-ken , 501-1193
Fax: 058-293-3346

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Gazette	WO 2014014067(PDF,373KB)