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

참여 물질

역할	이름	HCID	투입량
반응물	Tetrahydrofuran	HCID 8028	—
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	Triethylamine	HCID 8471	—
생성물	tert-Butyl [3-({2-[(tert-butoxycarbonyl)amino]-5-nitrophenyl}ethynyl)phenyl]carbamate	HCID 57962078	80%

반응 조건

온도	65 °C

반응 단계

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.

출처 및 근거

DOI	10.6084/m9.figshare.5104873.v1
특허 번호	US08871753B2
출처 데이터셋	uspto-grants-2014_10
ORD ID	ord-c82fa81207d14310b0474358618309e4
출처 메모	uspto-grants-2014_10