Potassium Iodide → (R)-N-(4-(5-((2-((tert-butyldimethylsilyl)oxy)-2-(8-hydroxy-2-oxo-1,2-dihydroquinolin-5-yl)ethyl)amino)pent-1-yn-1-yl)phenyl)-2,2,2-trifluoroacetamide

참여 물질

역할	이름	HCID	투입량
반응물	Potassium Iodide	HCID 4875	—
반응물	Diisopropylethylamine	HCID 81531	—
반응물	N-(4(5-bromopent-1-yn-1-yl)phenyl)-2,2,2-trifluoroacetamide	HCID 56923688	—
반응물	(R)-5-(2-Amino-1-((tert-butyldimethylsilyl)oxy)ethyl)-8-hydroxyquinolin-2(1H)-one	HCID 59023604	—
용매	Dimethylformamide	HCID 6228	—
생성물	(R)-N-(4-(5-((2-((tert-butyldimethylsilyl)oxy)-2-(8-hydroxy-2-oxo-1,2-dihydroquinolin-5-yl)ethyl)amino)pent-1-yn-1-yl)phenyl)-2,2,2-trifluoroacetamide	HCID 58505275	90.2%

반응 조건

온도	55 °C

반응 단계

A mixture of Intermediate 26 (0.33 g, 1.0 mmol) and Intermediate 2 (0.40 g, 1.2 mmol) in DMF (5 mL) was treated with N,N-diisopropylethylamine (DIEA, 0.25 mL, 1.5 mmol) and catalytic potassium iodide. The mixture was heated overnight in a 55° C. oil bath. The mixture was concentrated under reduced pressure and purified via automated flash silica gel chromatography, using a 12 g Isco RediSep flash column (dichloromethane/methanol/ammonium hydroxide). Concentration of the desired fractions under reduced pressure provided the title compound (0.53 g, 90%). ES/MS calcd. for C30H37F3N3O4Si+588.3. found m/z=588.4 (M+H)+.

출처 및 근거

DOI	10.6084/m9.figshare.5104873.v1
특허 번호	US08367829B2
출처 데이터셋	uspto-grants-2013_02
ORD ID	ord-fcb9c921f2614ef5a567a2b7543c76a5
출처 메모	uspto-grants-2013_02