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【结 构 式】

【分子编号】30940

【品名】2-[(E)-2-(1-methyl-1H-indol-2-yl)ethenyl]phenol

【CA登记号】

【 分 子 式 】C17H15NO

【 分 子 量 】249.31224

【元素组成】C 81.9% H 6.06% N 5.62% O 6.42%

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:(III)

The condensation of 1-methylindole-2-carbaldehyde (I) with 2-hydroxybenzyl triphenylphosphonium bromide (II) by means of BuLi in THF gives the vinyl derivative (III), which is condensed with (R)(+)-methyl lactate (IV) by means of DEAD and PPh3 in THF yielding the chiral ether derivative (V). The reduction of the carboxylate group of (V) with DIBAL in THF affords the expected chiral propanol derivative (VI), which is cyclized with N-methylmaleimide (VII) by heating at 180 C and aromatized with DDQ giving the pyrrolocarbazole (VIII). The reaction of the hydroxy group of (VIII) with tosyl chloride and pyridine yields the corresponding tosylate (IX), which is finally condensed with dimethylamine in hot DMF.

1 Ikuina, Y.; et al.; Synthesis and structure-activity relationships of pyrrolocarbazole derivatives possessing thrombopoietic activity. 217th ACS Natl Meet (March 21 1999, Anaheim) 1999, Abst MEDI 089.
2 Ikuina, Y.; Murakata, C.; Saitoh, Y.; Shiotsu, Y.; Iida, T.; Tamaoki, T.; Yamashita, K.; Akinaga, S. (Kyowa Hakko Kogyo Co., Ltd.); Pyrrolocarbazole derivs.. EP 0768311; US 5728709; WO 9628447 .
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) 30938 1-methyl-1H-indole-2-carbaldehyde C10H9NO 详情 详情
(II) 30939 (2-hydroxybenzyl)(triphenyl)phosphonium bromide 70340-04-4 C25H22BrOP 详情 详情
(III) 30940 2-[(E)-2-(1-methyl-1H-indol-2-yl)ethenyl]phenol C17H15NO 详情 详情
(IV) 11591 methyl (2R)-2-hydroxypropanoate 17392-83-5 C4H8O3 详情 详情
(V) 30941 methyl (2S)-2-[2-[(E)-2-(1-methyl-1H-indol-2-yl)ethenyl]phenoxy]propanoate C21H21NO3 详情 详情
(VI) 30942 (2S)-2-[2-[(E)-2-(1-methyl-1H-indol-2-yl)ethenyl]phenoxy]-1-propanol C20H21NO2 详情 详情
(VII) 30943 1-methyl-1H-pyrrole-2,5-dione 930-88-1 C5H5NO2 详情 详情
(VIII) 30944 4-(2-[[(1S)-2-hydroxy-1-methylethyl]oxy]phenyl)-2,6-dimethylpyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione C25H22N2O4 详情 详情
(IX) 30945 (2S)-2-[2-(2,6-dimethyl-1,3-dioxo-1,2,3,6-tetrahydropyrrolo[3,4-c]carbazol-4-yl)phenoxy]propyl 4-methylbenzenesulfonate C32H28N2O6S 详情 详情

合成路线2

该中间体在本合成路线中的序号:(III)

The condensation of 1-methylindole-2-carbaldehyde (I) with 2-hydroxybenzyl triphenylphosphonium bromide (II) by means of BuLi in THF gives the vinyl derivative (III), which is condensed with (rac)-methyl lactate (IV) by means of DEAD and PPh3 in THF yielding the ether derivative (V). The reduction of the carboxylate group of (V) with DIBAL in THF affords the expected propanol derivative (VI), which is cyclized with N-methylmaleimide (VII) by heating at 180 C and aromatized with DDQ giving the pyrrolocarbazole (VIII). The reaction of the hydroxy group of (VIII) with tosyl chloride and pyridine yields the corresponding tosylate (IX), which is finally condensed with dimethylamine in hot DMF.

1 Ikuina, Y.; et al.; Synthesis and structure-activity relationships of pyrrolocarbazole derivatives possessing thrombopoietic activity. 217th ACS Natl Meet (March 21 1999, Anaheim) 1999, Abst MEDI 089.
2 Ikuina, Y.; Murakata, C.; Saitoh, Y.; Shiotsu, Y.; Iida, T.; Tamaoki, T.; Yamashita, K.; Akinaga, S. (Kyowa Hakko Kogyo Co., Ltd.); Pyrrolocarbazole derivs.. EP 0768311; US 5728709; WO 9628447 .
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) 30938 1-methyl-1H-indole-2-carbaldehyde C10H9NO 详情 详情
(II) 30939 (2-hydroxybenzyl)(triphenyl)phosphonium bromide 70340-04-4 C25H22BrOP 详情 详情
(III) 30940 2-[(E)-2-(1-methyl-1H-indol-2-yl)ethenyl]phenol C17H15NO 详情 详情
(IV) 30946 methyl 2-hydroxypropanoate C4H8O3 详情 详情
(V) 30947 methyl 2-[2-[(E)-2-(1-methyl-1H-indol-2-yl)ethenyl]phenoxy]propanoate C21H21NO3 详情 详情
(VI) 30948 2-[2-[(E)-2-(1-methyl-1H-indol-2-yl)ethenyl]phenoxy]-1-propanol C20H21NO2 详情 详情
(VII) 30943 1-methyl-1H-pyrrole-2,5-dione 930-88-1 C5H5NO2 详情 详情
(VIII) 30949 4-[2-(2-hydroxy-1-methylethoxy)phenyl]-2,6-dimethylpyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione C25H22N2O4 详情 详情
(IX) 30950 2-[2-(2,6-dimethyl-1,3-dioxo-1,2,3,6-tetrahydropyrrolo[3,4-c]carbazol-4-yl)phenoxy]propyl 4-methylbenzenesulfonate C32H28N2O6S 详情 详情
Extended Information