Triethylamine → N-Isopropyl-1-[3-(3-hydroxy-3-phenylbut-1-ynyl)phenyl]-1,4-dihydro [1,8]naphthyridin-4-one-3-carboxamide

関与物質

役割	名称	HCID	仕込み量
反応物	Triethylamine	HCID 8471	—
反応物	3-Hydroxy-3-phenyl-1-butyne	HCID 92098	—
反応物	1-(3-bromophenyl)-N-isopropyl-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxamide	HCID 12991318	—
触媒	Palladium Chloride	HCID 24290	—
触媒	Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)	HCID 24350	—
触媒	Ferrocene-1,1'-bis-(diphenylphosphine)	HCID 635956	—
溶媒	Dimethylformamide	HCID 6228	—
生成物	N-Isopropyl-1-[3-(3-hydroxy-3-phenylbut-1-ynyl)phenyl]-1,4-dihydro [1,8]naphthyridin-4-one-3-carboxamide	HCID 10161154	—

反応条件

温度	85 °C

反応手順

A mixture of N-isopropyl-1-(3-bromophenyl)-1,4-dihydro[1,8]naphthyridin-4-one-3-carboxamide from Step 4 of EXAMPLE 1, 2-phenyl-3-butyn-2-ol (2 eq), triethylamine (1.66 eq), bis(diphenylphosphino)ferrocene]dichloropalladium(II) (0.05 eq), and copper(I) iodide (5 mg/mmol) in DMF (20 ml/mmol) was heated at 85° C. for 18 hours. After cooling to room temperature, the resulting mixture was quenched with saturated aqueous ammonium chloride solution and partitioned between ethyl acetate and water. The crude product from the organic phase was chromatographed on silica gel eluting with 20% ether in methylene chloride. The purified product was stirred in ether at room temperature for 3 hours and filtered to afford the title compound as a white solid.

情報源と証拠

DOI	10.6084/m9.figshare.5104873.v1
特許番号	US06743802B2
出典データセット	uspto-grants-2004_06
ORD ID	ord-dd67d90dc91049d59b4870fc9e136467
出典メモ	uspto-grants-2004_06