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

참여 물질

역할	이름	HCID	투입량
반응물	Dimethyl Sulfoxide	HCID 679	—
반응물	Potassium Acetate	HCID 517044	—
반응물	Bis(neopentyl glycolato)diboron	HCID 2734316	—
반응물	tert-butyl-N-[1-[[5-bromo-6-(2-phenylethynyl)pyridin-2-yl]amino]-1-oxo-propan-2-yl]-N-methylcarbamate	HCID 86694372	—
촉매	Palladium Chloride	HCID 24290	—
촉매	Ferrocene-1,1'-bis-(diphenylphosphine)	HCID 635956	—
용매	Water	HCID 962	—
생성물	[6-[2-[Methyl-[(2-methylpropan-2-yl)oxycarbonyl]amino]propanoylamino]-2-(2-phenylethynyl)pyridin-3-yl]boronic acid	HCID 89764967	—

반응 조건

온도	65 °C

반응 단계

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).

출처 및 근거

DOI	10.6084/m9.figshare.5104873.v1
특허 번호	US08859541B2
출처 데이터셋	uspto-grants-2014_10
ORD ID	ord-9051c5d5e0f34b2683364f12abbee8e0
출처 메모	uspto-grants-2014_10