Potassium Acetate → 1-(4-(2-Hydroxy-2-methylpropoxy)-3-methoxyphenyl)-2-oxo-1,2-dihydropyridin-4-ylboronic acid

참여 물질

역할	이름	HCID	투입량
반응물	Potassium Acetate	HCID 517044	—
반응물	Bis(pinacolato)diborane	HCID 2733548	—
반응물	2-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenyl	HCID 11155794	—
반응물	4-chloro-1-(4-(2-hydroxy-2-methylpropoxy)-3-methoxyphenyl)pyridin-2(1H)-one	HCID 58580294	—
촉매	Palladium, tris[mu-[(1,2-eta:4,5-eta)-(1E,4E)-1,5-diphenyl-1,4-pentadien-3-one]]di-, compd. with trichloromethane (1:1)	HCID 11029508	—
용매	1,4-Dioxane	HCID 31275	—
생성물	1-(4-(2-Hydroxy-2-methylpropoxy)-3-methoxyphenyl)-2-oxo-1,2-dihydropyridin-4-ylboronic acid	HCID 58580210	36.3%

반응 단계

A mixture of 4-chloro-1-(4-(2-hydroxy-2-methylpropoxy)-3-methoxyphenyl)pyridin-2(1H)-one Part D of procedure 9 (300 mg, 0.93 mmol), 4,4,4′, 4′,5,5,5′,5′-octamethyl-2,2′-bi(1,3,2-dioxaborolane) (706 mg, 2.78 mmol), potassium acetate (273 mg, 2.78 mmol), TRIS(DIBENZYLIDENEACETONE)-DIPALLADIUM(0)-CHLOROFORM ADDUCT (67 mg, 0.06 mmol), and X-Phos (133 mg, 0.28 mmol) in Dioxane (6 mL) was stirred at 90° C. for 18 hours (Mullen et al, JOC, 2008, 73 (23) 9207-9213). The reaction was filtered and concentrated. The crude was purified using ISCO flash chromatography (silica gel/methylene chloride/methanol 100:0 to 90:10 gradient) to afford the desired product 1-(4-(2-hydroxy-2-methylpropoxy)-3-methoxyphenyl)-2-oxo-1,2-dihydropyridin-4-ylboronic acid 12A (112 mg, 0.336 minol, 36.3% yield) as a brown solid. LC/MS 334 (M+H)+, tR 0.59 min (method 5)

출처 및 근거

DOI	10.6084/m9.figshare.5104873.v1
특허 번호	US08563583B2
출처 데이터셋	uspto-grants-2013_10
ORD ID	ord-8eb931179ec64d0ca10fbbba76dbb56d
출처 메모	uspto-grants-2013_10