Tetrahydrofuran → tert-Butyl [3-({2-[(tert-butoxycarbonyl)amino]-5-nitrophenyl}ethynyl)phenyl]carbamate

関与物質

役割	名称	HCID	仕込み量
反応物	Tetrahydrofuran	HCID 8028	—
反応物	Tert-butyl 4-nitro-2-iodophenylcarbamate	HCID 7098713	—
反応物	tert-Butyl 3-ethynylphenylcarbamate	HCID 11275982	—
触媒	Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)	HCID 24350	—
触媒	HCID 178418476	HCID 178418476	—
溶媒	Triethylamine	HCID 8471	—
生成物	tert-Butyl [3-({2-[(tert-butoxycarbonyl)amino]-5-nitrophenyl}ethynyl)phenyl]carbamate	HCID 57962078	80%

反応条件

温度	65 °C

反応手順

Into the reaction flask was added tert-butyl (2-iodo-4-nitrophenyl)carbamate (2.71 g, 7.44 mmol), copper(I) iodide (0.057 g, 0.30 mmol), bis(triphenylphosphine)palladium(II) chloride (0.21 g, 0.30 mmol), tetrahydrofuran (20 mL), and triethylamine (1.1 mL). It was stirred under N2 bubbling for 5 min. tert-Butyl (3-ethynylphenyl)carbamate (1.62 g, 7.44 mmol) was then added. The reaction mixture was stirred at 65° C. for 3 h. After concentration, the residue was diluted with EtOAc and water. The aqueous layer was extracted again with fresh EtOAc. The organic layers were combined and dried over Na2SO4. After filtration and concentration, the crude was purified by silica gel column chromatography to give the desired product (2.7 g, 80%). LCMS for C24H28N3O6 (M+H)+: m/z=454.1.

情報源と証拠

DOI	10.6084/m9.figshare.5104873.v1
特許番号	US08871753B2
出典データセット	uspto-grants-2014_10
ORD ID	ord-c82fa81207d14310b0474358618309e4
出典メモ	uspto-grants-2014_10