4-(2-bromoethyl)-1,3-dihydro-2H-indol-2-one -Drug Synthesis Database

【结构式】

【分子编号】34871

【品名】4-(2-bromoethyl)-1,3-dihydro-2H-indol-2-one

【CA登记号】

【分子式】C₁₀H₁₀BrNO

【分子量】240.09954

【元素组成】C 50.03% H 4.2% Br 33.28% N 5.83% O 6.66%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号：(XII)

The bromination of 3,4-dihydro-1H-2-benzopyran (VII) with Br2 gives the 1-bromo derivative (VIII), which, without isolation, is treated with hot HBr yielding 2-(2-bromoethyl)benzaldehyde (IX). The condensation of (IX) with nitromethane in acidic medium affords the nitrostyrene (X), which is cyclized with treatment with FeCl3 and acetyl chloride giving 4-(2-bromoethyl)-3-chloroindolin-2-one (XI). The dechlorination of (XI) with NaH2PO2 over Pd/C yields 4-(2-bromoethyl)indolin-2-one (XII), which is finally condensed with dipropylamine (II).

参考文献中间体

合成目标

【1】 Hayler, J.D.; et al.; Development of large-scale syntheses or ropinirole in the pursuit of a manufacturing process. Org Process Res Dev 1998, 2, 1, 3.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
	19273	acetyl chloride	75-36-5	C₂H₃ClO	详情	详情
	39563	nitromethane	75-52-5	CH₃NO₂	详情	详情
(II)	21856	N,N-dipropylamine; N-propyl-1-propanamine	142-84-7	C₆H₁₅N	详情	详情
(VII)	34866	3,4-dihydro-1H-isochromene	493-05-0	C₉H₁₀O	详情	详情
(VIII)	34867	1-bromo-3,4-dihydro-1H-isochromene		C₉H₉BrO	详情	详情
(IX)	34868	2-(2-bromoethyl)benzaldehyde		C₉H₉BrO	详情	详情
(X)	34869	1-(2-bromoethyl)-2-[(E)-2-nitroethenyl]benzene		C₁₀H₁₀BrNO₂	详情	详情
(XI)	34870	4-(2-bromoethyl)-3-chloro-1,3-dihydro-2H-indol-2-one		C₁₀H₉BrClNO	详情	详情
(XII)	34871	4-(2-bromoethyl)-1,3-dihydro-2H-indol-2-one		C₁₀H₁₀BrNO	详情	详情

Extended Information