Cesium carbonate → 3-Bromo-5-{6-oxo-8-thia-5-azatricyclo[7.4.0.02,7]trideca-1(9),2(7)-dien-5-yl}pyridine-4-carbaldehyde

関与物質

役割	名称	HCID	仕込み量
反応物	Cesium carbonate	HCID 10796	—
反応物	1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)	HCID 636044	—
反応物	3,5-Dibromo-4-pyridinecarboxaldehyde	HCID 2762998	—
反応物	3,4,5,6,7,8-Hexahydrobenzo[4,5]thieno[2,3-c]pyridin-1(2H)-one	HCID 20899754	—
触媒	Bis(dibenzylideneacetone)palladium	HCID 9811564	—
溶媒	1,4-Dioxane	HCID 31275	—
生成物	3-Bromo-5-{6-oxo-8-thia-5-azatricyclo[7.4.0.02,7]trideca-1(9),2(7)-dien-5-yl}pyridine-4-carbaldehyde	HCID 86684175	70%

反応条件

温度	100 °C

反応手順

To a 100-mL single-neck round-bottomed flask equipped with a magnetic stirrer and reflux condenser was charged with 1,4-dioxane (15 mL), 3,5-dibromoisonicotin-aldehyde (400 mg, 1.5 mmol), 8-thia-5-azatricyclo[7.4.0.02,7]trideca-1(9),2(7)-dien-6-one 105e (146 mg, 0.76 mmol), and cesium carbonate (176 mg, 1.5 mmol). Xantphos (40 mg, 0.08 mmol) and Pd2(dba)3 (70 mg, 0.08 mmol) were added, and the reaction mixture was heated at 100° C. for 5 h. After this time the reaction was cooled to room temperature and filtered. The filtrate was concentrated under reduced pressure and the residue was purified on flash column eluting with DCM:MeOH (20:1) to afford 105f (200 mg, 70%). MS: [M+H]+ 377.

情報源と証拠

DOI	10.6084/m9.figshare.5104873.v1
特許番号	US09238655B2
出典データセット	uspto-grants-2016_01
ORD ID	ord-ed0642e33c244b1eb72b9d370d83d1d9
出典メモ	uspto-grants-2016_01