Cesium fluoride → 2-(4-(1,3-Dioxan-2-yl)-2-fluorophenyl)-5-(1-(4-(benzyloxy)phenyl)vinyl)thiazolo[5,4-b]pyridine

참여 물질

역할	이름	HCID	투입량
반응물	Cesium fluoride	HCID 25953	—
반응물	{1-[4-(Benzyloxy)phenyl]ethenyl}(tributyl)stannane	HCID 18436367	—
반응물	2-(4-(1,3-Dioxan-2-yl)-2-fluorophenyl)-5-chlorothiazolo[5,4-b]pyridine	HCID 59174862	—
촉매	Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)	HCID 24350	—
촉매	Tetrakis(triphenylphosphine)palladium	HCID 11979704	—
용매	Dimethylformamide	HCID 6228	—
용매	Ethyl Acetate	HCID 8857	—
생성물	2-(4-(1,3-Dioxan-2-yl)-2-fluorophenyl)-5-(1-(4-(benzyloxy)phenyl)vinyl)thiazolo[5,4-b]pyridine	HCID 67111438	—

반응 조건

온도	55 °C

반응 단계

A slurry of cesium fluoride (0.325 g, 2.14 mmol), CuI 0.0271 g, 0.143 mmol), tetrakis(triphenylphosphine) palladium (0) (0.0824 g, 0.0713 mmol), 2-(4-(1,3-dioxan-2-yl)-2-fluorophenyl)-5-chlorothiazolo[5,4-b]pyridine (0.500 g, 1.43 mmol), and crude (1-(4-(benzyloxy)-phenyl)vinyl)tributylstannane (1.07 g, 2.14 mmol) in 5 mL DMF was flushed with argon, sealed, and heated to 55° C. overnight. The reaction mixture was diluted with EA, filtered through celite, rinsing with EA. The filtrate was washed with water, brine, dried over sodium sulfate, filtered, and concentrated. The residue was adsorbed onto 4 g silica gel from DCM, concentrated, and purified by ISCO 40 g, 0-100% EA/hexanes to give 2-(4-(1,3-dioxan-2-yl)-2-fluorophenyl)-5-(1-(4-(benzyloxy)phenyl)vinyl)thiazolo[5,4-b]pyridine as an orange solid. MS (ESI) m/z: calculated: 524.2; Observed: 525.1 (M++1).

출처 및 근거

DOI	10.6084/m9.figshare.5104873.v1
특허 번호	US07842685B2
출처 데이터셋	uspto-grants-2010_11
ORD ID	ord-ab63040e05d24648a271a578f48bba7e
출처 메모	uspto-grants-2010_11