5-methoxy-1-(phenylsulfonyl)-1H-indole; methyl 1-(phenylsulfonyl)-1H-indol-5-yl ether -Drug Synthesis Database

【结构式】

【分子编号】57928

【品名】5-methoxy-1-(phenylsulfonyl)-1H-indole; methyl 1-(phenylsulfonyl)-1H-indol-5-yl ether

【CA登记号】

【分子式】C₁₅H₁₃NO₃S

【分子量】287.33916

【元素组成】C 62.7% H 4.56% N 4.87% O 16.7% S 11.16%

与该中间体有关的原料药合成路线共 2 条

合成路线1 合成路线2

合成路线1

该中间体在本合成路线中的序号：(III)

Protection of 5-methoxyindole (I) with benzenesulfonyl chloride (II) in the presence of NaH affords the N-sulfonyl indole (III). Acylation of the 2-lithio derivative of (III) with benzoyl chloride (IV) gives rise to ketone (V). Finally, removal of the phenylsulfonyl protecting group of (V) is achieved by either basic hydrolysis or by treatment with tetrabutylammonium fluoride.

参考文献中间体

合成目标

【1】 Hufsky, H.; Pongratz, H.; Mahboobi, S.; et al.; Synthetic 2-aroylindole derivatives as a new class of potent tubulin-inhibitory, antimitotic agents. J Med Chem 2001, 44, 26, 4535.
【2】 Teller, S.; Pongratz, H.; Mahboobi, S.; et al.; Bis(1H-2-indolyl) methanones as a novel class of inhibitors of the platelet-derived growth factor receptor kinase. J Med Chem 2002, 45, 5, 1002.
【3】 Burger, A.; Mahboobi, S.; Pongratz, H.; Hufsky, H.; Böhmer, F.-D.; Beckers, T.; Klenner, T.; Baasner, S.; Frieser, M.; Hockemeyer, J.; Fiebig, H.-H. (Asta Medica AG); 2-Acyl indol derivs. and their use as anti-tumour agents. DE 10020852; WO 0182909 .

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(I)	25902	1H-Indol-5-yl methyl ether; 5-Methoxy-1H-indole; 5-Methoxyindole	1006-94-6	C₉H₉NO	详情	详情
(II)	14713	benzenesulfonyl chloride	98-09-9	C₆H₅ClO₂S	详情	详情
(III)	57928	5-methoxy-1-(phenylsulfonyl)-1H-indole; methyl 1-(phenylsulfonyl)-1H-indol-5-yl ether		C₁₅H₁₃NO₃S	详情	详情
(IV)	10463	Benzoyl chloride	98-88-4	C₇H₅ClO	详情	详情
(V)	57929	[5-methoxy-1-(phenylsulfonyl)-1H-indol-2-yl](phenyl)methanone		C₂₂H₁₇NO₄S	详情	详情

合成路线2

该中间体在本合成路线中的序号：(I)

In a related method, the 2-lithio derivative of 5-methoxy-1-(phenylsulfonyl)indole (I) is condensed with benzaldehyde (II) to produce carbinol (III). Subsequent oxidation of (III) to the corresponding ketone (IV) is accomplished by treatment with pyridinium dichromate (PDC) in the presence of pyridinium trifluoroacetate (PTFA). Finally, the N-phenylsulfonyl group of (IV) is deprotected by treatment with tetrabutylammonium fluoride.

参考文献中间体

合成目标

【1】 Teller, S.; Pongratz, H.; Mahboobi, S.; et al.; Bis(1H-2-indolyl) methanones as a novel class of inhibitors of the platelet-derived growth factor receptor kinase. J Med Chem 2002, 45, 5, 1002.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(I)	57928	5-methoxy-1-(phenylsulfonyl)-1H-indole; methyl 1-(phenylsulfonyl)-1H-indol-5-yl ether		C₁₅H₁₃NO₃S	详情	详情
(II)	10498	Benzaldehyde;Benzoic aldehyde;Phenylmethanal	100-52-7	C₇H₆O	详情	详情
(III)	57930	[5-methoxy-1-(phenylsulfonyl)-1H-indol-2-yl](phenyl)methanol		C₂₂H₁₉NO₄S	详情	详情
(IV)	57929	[5-methoxy-1-(phenylsulfonyl)-1H-indol-2-yl](phenyl)methanone		C₂₂H₁₇NO₄S	详情	详情

Extended Information