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【结 构 式】

【分子编号】61317

【品名】2-(4-bromophenyl)-6-(ethylsulfanyl)-4H-thiopyran-4-one

【CA登记号】

【 分 子 式 】C13H11BrOS2

【 分 子 量 】327.26574

【元素组成】C 47.71% H 3.39% Br 24.42% O 4.89% S 19.6%

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:(IV)

Claisen condensation of 4-bromoacetophenone (I) with ethyl acetate provides diketone (II). Subsequent reaction of (II) with carbon disulfide in the presence of LDA leads to thiopyranone thiol (III). Alkylation of thiol (III) with iodoethane and K2CO3 affords sulfide (IV), which is further oxidized to sulfoxide (V) by means of mCPBA. Displacement of either sulfide (IV) or sulfoxide (V) with morpholine gives rise to the morpholinyl thiopyranone (VI). Finally, Suzuki coupling between aryl bromide (VI) and 2-naphthaleneboronic acid (VII) produces the target compound

1 Griffin, R.J.; Combinatorial methods for identifying antitumour kinase inhibitors. Eur J Cancer 2002, 38, Suppl. 7.
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) 25421 1-(4-bromophenyl)-1-ethanone 99-90-1 C8H7BrO 详情 详情
(II) 61315 1-(4-bromophenyl)-1,3-butanedione C10H9BrO2 详情 详情
(III) 61316 2-(4-bromophenyl)-6-sulfanyl-4H-thiopyran-4-one C11H7BrOS2 详情 详情
(IV) 61317 2-(4-bromophenyl)-6-(ethylsulfanyl)-4H-thiopyran-4-one C13H11BrOS2 详情 详情
(V) 61318 2-(4-bromophenyl)-6-(ethylsulfinyl)-4H-thiopyran-4-one C13H11BrO2S2 详情 详情
(VI) 61319 2-(4-bromophenyl)-6-(4-morpholinyl)-4H-thiopyran-4-one C15H14BrNO2S 详情 详情
(VII) 27703 1-naphthylboronic acid 13922-41-3 C10H9BO2 详情 详情
Extended Information