Dimethyl Sulfoxide → [6-[2-[Methyl-[(2-methylpropan-2-yl)oxycarbonyl]amino]propanoylamino]-2-(2-phenylethynyl)pyridin-3-yl]boronic acid

関与物質

役割	名称	HCID	仕込み量
反応物	Dimethyl Sulfoxide	HCID 679	—
反応物	Potassium Acetate	HCID 517044	—
反応物	Bis(neopentyl glycolato)diboron	HCID 2734316	—
反応物	tert-butyl-N-[1-[[5-bromo-6-(2-phenylethynyl)pyridin-2-yl]amino]-1-oxo-propan-2-yl]-N-methylcarbamate	HCID 86694372	—
触媒	Palladium Chloride	HCID 24290	—
触媒	Ferrocene-1,1'-bis-(diphenylphosphine)	HCID 635956	—
溶媒	Water	HCID 962	—
生成物	[6-[2-[Methyl-[(2-methylpropan-2-yl)oxycarbonyl]amino]propanoylamino]-2-(2-phenylethynyl)pyridin-3-yl]boronic acid	HCID 89764967	—

反応条件

温度	65 °C

反応手順

A mixture of tert-butyl-N-[1-[[5-bromo-6-(2-phenylethynyl)pyridin-2-yl]amino]-1-oxopropan-2-yl]-N-methylcarbamate C2a (2.5 g, 5.45 mmol), bis(neopentyl glycolato)diboron (2.46 g, 10.9 mmol), KOAc (1.61 g, 16.4 mmol), 1,1′-Bis(diphenylphosphino)ferrocene]-dichloropalladium(II) (399 mg, 0.55 mmol) and DMSO (20 ml) is stirred under argon atmosphere for 39 h at 65° C. The mixture is diluted with water and extracted with DCM. The combined organic layers are dried over MgSO4, concentrated in vacuo and the product purified by RP HPLC. Yield: 1.73 g (75%). HPLC-MS: M+H=424; tR=1.59 min (*Method—5).

情報源と証拠

DOI	10.6084/m9.figshare.5104873.v1
特許番号	US08859541B2
出典データセット	uspto-grants-2014_10
ORD ID	ord-9051c5d5e0f34b2683364f12abbee8e0
出典メモ	uspto-grants-2014_10