Iodoethane → 3-[4-(benzyloxy)phenyl]-6-chloro-1-ethyl-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one

참여 물질

역할	이름	HCID	투입량
반응물	Iodoethane	HCID 6340	—
반응물	4-Benzyloxyaniline	HCID 22860	—
반응물	Sodium hydride	HCID 24758	—
반응물	1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)	HCID 636044	—
반응물	Calcium Chloride	HCID 5284359	—
반응물	Sodium t-butoxide	HCID 23676156	—
반응물	Tert-butyl 2,5-dichloropyridin-3-ylcarbamate	HCID 86660673	—
촉매	Bis(dibenzylideneacetone)palladium	HCID 9811564	—
용매	Methanol	HCID 887	—
용매	Toluene	HCID 1140	—
용매	Isopropanol	HCID 3776	—
용매	Dimethylformamide	HCID 6228	—
생성물	3-[4-(benzyloxy)phenyl]-6-chloro-1-ethyl-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one	HCID 58577370	247.5%

반응 조건

온도	100 °C

반응 단계

The mixture of tert-butyl (2,5-dichloropyridin-3-yl)carbamate (7.0 g), 4-(benzyloxy)aniline (7.95 g), 9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene (1.231 g), Pd2(dba)3 (0.974 g) and sodium tert-butoxide (3.58 g) in toluene (160 mL)-2-propanol (40.0 mL) was stirred at 100° C. under Ar overnight. The reaction mixture was concentrated in vacuo. The residue was purified by column chromatography (silica gel, eluted with 0%-100% EtOAc in hexane) to give intermediate. To the intermediate in DMF (100 mL) were added NaH (3.19 g) and ethyl iodide (20.75 g). The mixture was stirred at room temperature under a dry atmosphere (CaCl2 tube) for 1 h. The reaction mixture was diluted with MeOH and concentrated in vacuo. The residue was purified by column chromatography (NH silica gel, eluted with 0%-50% EtOAc in hexane) to give 3-[4-(benzyloxy)phenyl]-6-chloro-1-ethyl-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one (2 g) as a colorless solid.

출처 및 근거

DOI	10.6084/m9.figshare.5104873.v1
특허 번호	US08563575B2
출처 데이터셋	uspto-grants-2013_10
ORD ID	ord-c99913e3fddd4c7bab334223fac7ed22
출처 메모	uspto-grants-2013_10