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【结 构 式】

【分子编号】60392

【品名】(E)-1-(5-fluoro-2-hydroxyphenyl)-3-[4-(methylsulfanyl)phenyl]-2-propen-1-one

【CA登记号】

【 分 子 式 】C16H13FO2S

【 分 子 量 】288.3424232

【元素组成】C 66.65% H 4.54% F 6.59% O 11.1% S 11.12%

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:(III)

Aldol condensation between 5'-fluoro-2'-hydroxyacetophenone (I) and 4-(methylthio)benzaldehyde (II) produces chalcone (III). Oxidative cyclization of (III) in hot DMSO in the presence of iodine leads to the flavone compound (IV). Further oxidation of the methylthio group of (IV) employing oxone furnishes sulfone (V). Conversion of flavone (V) into the 3-iodo derivative (VI) is carried out by treatment with iodine and bis(trifluoroacetoxy)iodobenzene. Finally, Suzuki coupling of the iodoflavone (VI) with lithium trimethoxy-3-pyridylboronate (VII) provides the desired 2,3-diaryl benzopyranone

1 Joo, Y.H.; Kim, J.K.; Kang, S-H.; Noh, M-S.; Ha, J-Y.; Choi, J.K.; Lim, K.M.; Lee, C.H.; Chung, S.; Diarylbenzopyran derivatives as a selective inhibitor of cyclooxygenase-2. 224th ACS Natl Meet (Aug 18 2002, Boston) 2002, Abst MEDI 313.
2 Kim, J.K.; Choi, J.K.; Lee, C.H.; Joo, Y.H.; Noh, M.-S.; Ha, J.-Y.; Lim, K.M.; Kang, S.-H. (Pacific Corp.); Diarylbenzopyran derivs. as cyclooxygenase-2 inhibitors. EP 1105384; JP 2002523410; US 6340694; WO 0010993 .
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) 60391 1-(5-fluoro-2-hydroxyphenyl)-1-ethanone 394-32-1 C8H7FO2 详情 详情
(II) 18815 4-(methylsulfanyl)benzaldehyde; 4-(methylmercapto)benzaldehyde 3446-89-7 C8H8OS 详情 详情
(III) 60392 (E)-1-(5-fluoro-2-hydroxyphenyl)-3-[4-(methylsulfanyl)phenyl]-2-propen-1-one C16H13FO2S 详情 详情
(IV) 60393 6-fluoro-2-[4-(methylsulfanyl)phenyl]-4H-chromen-4-one C16H11FO2S 详情 详情
(V) 60394 6-fluoro-2-[4-(methylsulfonyl)phenyl]-4H-chromen-4-one C16H11FO4S 详情 详情
(VI) 60395 6-fluoro-3-iodo-2-[4-(methylsulfonyl)phenyl]-4H-chromen-4-one C16H10FIO4S 详情 详情
(VII) 30006 Trimethoxy(3-pyridyl)boranuide lithium salt C8H13BLiNO3 详情 详情
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