Dichloromethane → 2-(7,7-dimethyl-1-oxo-3,4,7,8-tetrahydro-1H-cyclopenta[4,5]pyrrolo[1,2-a]pyrazin-2(6H)-yl)-4-fluoro-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl acetate

関与物質

役割	名称	HCID	仕込み量
反応物	Dichloromethane	HCID 6344	—
反応物	Potassium Acetate	HCID 517044	—
反応物	Bis(pinacolato)diborane	HCID 2733548	—
反応物	HCID 67016205	HCID 67016205	—
反応物	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	—
触媒	Ferrocene-1,1'-bis-(diphenylphosphine)	HCID 635956	—
溶媒	1,4-Dioxane	HCID 31275	—
生成物	2-(7,7-dimethyl-1-oxo-3,4,7,8-tetrahydro-1H-cyclopenta[4,5]pyrrolo[1,2-a]pyrazin-2(6H)-yl)-4-fluoro-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl acetate	HCID 67016232	—

反応条件

温度	100 °C

反応手順

Compound 110g was synthesized using the same procedure as 103g, except using 110f (450 mg, 1.0 mmol), 4,4,4′,4′,5,5,5′,5′-octamethyl-2,2′-bi(1,3,2-dioxaborolane) (635 mg, 2.5 mmol), potassium acetate (393 mg, 4.0 mmol), bis(diphenylphosphino)-ferrocene]dichloropalladium(II) complex with CH2Cl2 (Pd Cl2dppf:CH2Cl2 (1:1), 66 mg, 0.08 mmol) and 1,4-dioxane (20 mL). The reaction mixture was heated at 100° C. for 5 h. The reaction mixture was cooled to room temperature and filtered through a pad of Celite 521. The filter cake was washed with Ethyl Acetate (2×25 mL), and the combined filtrates were concentrated to dryness under reduced pressure to afford 110g (quantitative yield) as black oil, which was used directly for the next step. MS (ESI+) m/z 497.3 (M+H).

情報源と証拠

DOI	10.6084/m9.figshare.5104873.v1
特許番号	US08722676B2
出典データセット	uspto-grants-2014_05
ORD ID	ord-35d836abbc364cf38075f13b43bd747b
出典メモ	uspto-grants-2014_05