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

참여 물질

역할	이름	HCID	투입량
반응물	Diisopropylethylamine	HCID 81531	—
반응물	Tert-butyl 4-nitro-2-iodophenylcarbamate	HCID 7098713	—
반응물	tert-Butyl 3-ethynylphenylcarbamate	HCID 11275982	—
촉매	Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)	HCID 24350	—
촉매	HCID 178418476	HCID 178418476	—
용매	Tetrahydrofuran	HCID 8028	—
생성물	tert-Butyl [3-({2-[(tert-butoxycarbonyl)amino]-5-nitrophenyl}ethynyl)phenyl]carbamate	HCID 57962078	85%

반응 조건

온도	20 °C

반응 단계

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.

출처 및 근거

DOI	10.6084/m9.figshare.5104873.v1
특허 번호	US08871753B2
출처 데이터셋	uspto-grants-2014_10
ORD ID	ord-885e2872087d49939c7838011470e71f
출처 메모	uspto-grants-2014_10