6-[4-(methylsulfanyl)phenyl]-1,3-benzodioxole-5-carbaldehyde -Drug Synthesis Database

【结构式】

【分子编号】64023

【品名】6-[4-(methylsulfanyl)phenyl]-1,3-benzodioxole-5-carbaldehyde

【CA登记号】

【分子式】C₁₅H₁₂O₃S

【分子量】272.32448

【元素组成】C 66.16% H 4.44% O 17.63% S 11.77%

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)

Piperonal (I) is brominated by means of Br2 in AcOH to produce (II). Subsequent Suzuki coupling of aryl bromide (II) with 4-(methylsulfanyl)benzeneboronic acid (III) furnishes adduct (IV). Addition of 3-fluorophenylmagnesium bromide (V) to aldehyde (IV) leads to carbinol (VI). The sulfide group is further oxidized to sulfone (VII) employing oxone in aqueous MeOH. Finally, oxidation of alcohol (VII) with pyridinium chlorochromate provides the target ketone. (1,2)

参考文献中间体

合成目标

【1】 Ezawa, M.; Khanapure, S.P.; Garvey, D.S.; Young, D.; Earl, R.; Gaston, R.; Fang, F.; Marek, P.; Shumway, M.; Trocha, M.; Tam, S.W.; Janero, D.R.; Letts, L.G.; Design and synthesis of novel benzo-dioxolane cyclooxygenase (COX-2) selective inhibitors. 225th ACS Natl Meet (March 23 2003, New Orleans) 2003, Abst MEDI 243.
【2】 Earl, R.A.; Garvey, D.S.; Khanapure, S.P.; Gaston, R.D.; Fang, X.; Ezawa, M. (NitroMed Inc.); Substd. aryl cpds. as novel cyclooxygenase-2 selective inhibitors, compsns. and methods of use. US 2002119977; WO 0260378 .

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)	10127	1,3-Benzodioxole-5-carbaldehyde; Heliotropine	120-57-0	C₈H₆O₃	详情	详情
(II)	46376	ethyl 3-(3-[2-[[(6-bromo-1,3-benzodioxol-5-yl)methyl](2-ethoxy-2-oxoacetyl)amino]phenyl]-3-oxopropyl)benzoate		C₃₀H₂₈BrNO₈	详情	详情
(III)	18561	4-(methylsulfanyl)phenylboronic acid	98546-51-1	C₇H₉BO₂S	详情	详情
(IV)	64023	6-[4-(methylsulfanyl)phenyl]-1,3-benzodioxole-5-carbaldehyde		C₁₅H₁₂O₃S	详情	详情
(V)	35384	bromo(3-fluorophenyl)magnesium		C₆H₄BrFMg	详情	详情
(VI)	64024	(3-fluorophenyl){6-[4-(methylsulfanyl)phenyl]-1,3-benzodioxol-5-yl}methanol		C₂₁H₁₇FO₃S	详情	详情
(VII)	64025	(3-fluorophenyl){6-[4-(methylsulfonyl)phenyl]-1,3-benzodioxol-5-yl}methanol		C₂₁H₁₇FO₅S	详情	详情

Extended Information