Dichloromethane → 6-(5-chloro-2-fluoropyridin-4-yl)-N2-((tetrahydro-2H-pyran-4-yl)methyl)pyrazine-2,3-diamine

https://huagongshe.com/reaction/1963939

참여 물질

역할	이름	HCID	투입량
반응물	Dichloromethane	HCID 6344	—
반응물	Sodium Carbonate	HCID 10340	—
반응물	(5-Chloro-2-fluoropyridin-4-yl)boronic acid	HCID 44754822	—
반응물	HCID 86626394	HCID 86626394	—
촉매	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
용매	1,2-Dimethoxyethane	HCID 8071	—
용매	Ethyl Acetate	HCID 8857	—
생성물	6-(5-chloro-2-fluoropyridin-4-yl)-N2-((tetrahydro-2H-pyran-4-yl)methyl)pyrazine-2,3-diamine	HCID 66937136	29%

반응 조건

온도	100 °C

반응 단계

To a degassed suspension of 6-bromo-N2-((tetrahydro-2H-pyran-4-yl)methyl)pyrazine-2,3-diamine (100 mg, 0.348 mmol), Na2CO3 (96 mg, 0.905 mmol) and 5-chloro-2-fluoropyridin-4-ylboronic acid (92 mg, 0.522 mmol) in DME (3 ml) was added PdCl2(dppf).CH2Cl2 adduct (22.75 mg, 0.028 mmol). The reaction mixture was capped in a flask and heated to 100° C. for 4 hr an oil bath. The reaction mixture was diluted with EtOAc and washed with H2O, sat NaCl. The organic layer was dried Na2SO4, filtered and concentrated. The crude was purified by column chromatography on silica gel (100% EtOAc/Hexane) to yield 6-(5-chloro-2-fluoropyridin-4-yl)-N2-((tetrahydro-2H-pyran-4-yl)methyl)pyrazine-2,3-diamine (34 mg, 0.101 mmol, 28.9% yield).). LCMS (m/z): 338.2 (MH+), retention time=0.65 min.

출처 및 근거

DOI	10.6084/m9.figshare.5104873.v1
특허 번호	US08415381B2
출처 데이터셋	uspto-grants-2013_04
ORD ID	ord-3bec5ea4a4b94fb8972a37219ccb866a
출처 메모	uspto-grants-2013_04