Diisopropylethylamine → 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	Diisopropylethylamine	HCID 81531	—
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	Tetrahydrofuran	HCID 8028	—
生成物	tert-Butyl [3-({2-[(tert-butoxycarbonyl)amino]-5-nitrophenyl}ethynyl)phenyl]carbamate	HCID 57962078	85%

反応条件

温度	20 °C

反応手順

A solution of tert-butyl (3-ethynylphenyl)carbamate (12.7 g, 58.5 mmol), tert-butyl (2-iodo-4-nitrophenyl)carbamate (14.2 g, 39.0 mmol), bis(triphenylphosphine)palladium(II) chloride (1.37 g, 1.95 mmol), and copper(I) iodide (371 mg, 1.95 mmol) in THF (200 mL) was treated with N,N-diisopropylethylamine (7.47 mL, 42.9 mmol) dropwise and stirred at 20° C. overnight. The reaction mixture was concentrated and diluted with water (200 mL) and ethyl acetate (200 mL). The organic layer was separated, washed with brine, dried with sodium sulfate, filtered, and concentrated to give a yellow/brown solid which was washed with ethyl acetate to give the desired product as light yellow solid (15 g, 85%). LCMS calculated for C24H27N3O6Na (M+Na)+: m/z=476.2.

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-885e2872087d49939c7838011470e71f
出典メモ	uspto-grants-2014_10