Cesium carbonate → 2-Bromo-4-fluoro-6-(9-oxo-4,4-dimethyl-1,10diazatricyclo[6.4.0.02,6]-dodeca-2(6),7-dien-10-yl)benzyl Acetate

https://huagongshe.com/reaction/519270

참여 물질

역할	이름	HCID	투입량
반응물	Cesium carbonate	HCID 10796	—
반응물	1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)	HCID 636044	—
반응물	7,7-dimethyl-3,4,7,8-tetrahydro-2H-cyclopenta[4,5]pyrrolo[1,2-a]pyrazin-1(6H)-one	HCID 58044202	—
반응물	2,6-Dibromo-4-fluorobenzyl acetate	HCID 67016593	—
촉매	Tris(dibenzylideneacetone) dipalladium	HCID 9832798	—
용매	Water	HCID 962	—
용매	Ethyl Acetate	HCID 8857	—
용매	1,4-Dioxane	HCID 31275	—
생성물	2-Bromo-4-fluoro-6-(9-oxo-4,4-dimethyl-1,10diazatricyclo[6.4.0.02,6]-dodeca-2(6),7-dien-10-yl)benzyl Acetate	HCID 67016304	56.3%

반응 조건

온도	100 °C

반응 단계

A sealed tube was equipped with a magnetic stirrer and charged with 103e (740 mg, 3.6 mmol), 2,6-dibromo-4-fluorobenzyl acetate 101c (2.4 g, 7.2 mmol) and cesium carbonate (2.6 g, 7.9 mmol) in 1,4-dioxane (36 mL). After bubbling nitrogen through the solution for 30 min, Xantphos (250 mg, 0.43 mmol) and tris(dibenzylideneacetone) dipalladium(0) (260 mg, 0.29 mmol) were added, and the reaction mixture was heated to 100° C. for 16 h. After this time, H2O (50 mL) and ethyl acetate (50 mL) were added. The aqueous layer was separated and extracted with ethyl acetate (2×50 mL). The combined organic extracts were washed with brine (100 mL) and dried over sodium sulfate. The resulting residue was purified by column chromatography eluting with a gradient of 100% hexanes-100% Ethyl acetate to afford a 56% yield (910 mg) of 103f.

출처 및 근거

DOI	10.6084/m9.figshare.5104873.v1
특허 번호	US09115152B2
출처 데이터셋	uspto-grants-2015_08
ORD ID	ord-0b0a482a5dc14cf0bece9f08b437d1e4
출처 메모	uspto-grants-2015_08