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【结 构 式】

【分子编号】38163

【品名】ethyl 5-nitro-1H-indole-2-carboxylate

【CA登记号】16732-57-3

【 分 子 式 】C11H10N2O4

【 分 子 量 】234.21148

【元素组成】C 56.41% H 4.3% N 11.96% O 27.32%

与该中间体有关的原料药合成路线共 2 条

合成路线1

该中间体在本合成路线中的序号:(I)

Ethyl 5-nitroindole-2-carboxylate (I) was hydrogenated over Pd/C to give amino indole (II), which was condensed with methanesulfonyl chloride, affording sulfonamide (III). Subsequent hydrolysis of the ester group of (III) furnished the intermediate indolecarboxylic acid (IV).

1 Romero, D.L.; Thomas, R.C.; May, P.D.; Poel, T.-J. (Pharmacia Corp.); Alkyl substd. piperadinyl and piperazinyl anti-AIDS cpds.. EP 0797576; JP 1998510530; US 5866589; WO 9618628 .
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) 38163 ethyl 5-nitro-1H-indole-2-carboxylate 16732-57-3 C11H10N2O4 详情 详情
(II) 38164 ethyl 5-amino-1H-indole-2-carboxylate C11H12N2O2 详情 详情
(III) 38165 ethyl 5-[(methylsulfonyl)amino]-1H-indole-2-carboxylate C12H14N2O4S 详情 详情
(IV) 38166 5-[(methylsulfonyl)amino]-1H-indole-2-carboxylic acid C10H10N2O4S 详情 详情

合成路线2

该中间体在本合成路线中的序号:(III)

Treatment of the cyclopropabenzindole derivative (CBI) (I) with hydrochloric acid in ethyl acetate affords the chloromethyl derivative (II). The final step is the condensation of (II) with the acid (VIII) by means of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide (EDCI) in DMF. The acid (VIII) was prepared as follows: Ethyl 5-nitroindole-2-carboxylate (III) is reductively transformed to its corresponding amine (IV) by hydrogenation over Pd/C. The amine (IV) is then converted to its acetamido ester (V) by treatment with acetic anhydride in ethyl acetate. Ester (V) is then hydrolyzed using NaOH to afford the corresponding acid (VI), which is coupled to amine (IV) in the presence of EDCI to yield ester (VII). Finally (VII) is converted to acid (VIII) by treatment with NaOH.

1 Wang, Y.; Ye, W.; Wright, S.C.; Larrick, J.W.; Wang, H.; Yuan, H.; Synthesis and preliminary biological evaluations of CC-1065 analogues: Effects of different linkers terminal amides on biological activity. J Med Chem 2000, 43, 8, 1541.
2 Larrick, J.W.; Wright, S.C.; Wang, Y. (Panorama Research, Inc.); DNA-binding indole derivs., their prodrugs and immunoconjugates as anticancer agents. WO 9744000 .
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) 40977 1-(chloromethyl)-2,3-dihydro-1H-benzo[e]indol-5-ol C13H12ClNO 详情 详情
(II) 40978 1,2,2a,3,9,9a-hexahydro-4H-benzo[e]cyclopropa[c]indol-4-one C13H13NO 详情 详情
(III) 38163 ethyl 5-nitro-1H-indole-2-carboxylate 16732-57-3 C11H10N2O4 详情 详情
(IV) 38164 ethyl 5-amino-1H-indole-2-carboxylate C11H12N2O2 详情 详情
(V) 40973 ethyl 5-(acetamido)-1H-indole-2-carboxylate C13H14N2O3 详情 详情
(VI) 40974 5-(acetamido)-1H-indole-2-carboxylic acid C11H10N2O3 详情 详情
(VII) 40975 ethyl 5-([[5-(acetamido)-1H-indol-2-yl]carbonyl]amino)-1H-indole-2-carboxylate C22H20N4O4 详情 详情
(VIII) 40976 5-([[5-(acetamido)-1H-indol-2-yl]carbonyl]amino)-1H-indole-2-carboxylic acid C20H16N4O4 详情 详情
Extended Information