2,4-di(tert-butyl)-6-iodophenol -Drug Synthesis Database

【结构式】

【分子编号】63974

【品名】2,4-di(tert-butyl)-6-iodophenol

【CA登记号】

【分子式】C₁₄H₂₁IO

【分子量】332.22461

【元素组成】C 50.61% H 6.37% I 38.2% O 4.82%

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：(I)

Alkylation of 2,4-di-tert-butyl-6-iodophenol (I) with bromopropane by means of NaH (1) or CsF (2) provides the corresponding propyl ether (II). Subsequent Suzuki coupling of aryl iodide (II) with 2-formylbenzeneboronic acid (III) leads to the biphenyl aldehyde (IV). This is then condensed with phosphonate (V) producing the dienoate ester (VI). Finally, the ethyl ester group of (VI) is hydrolyzed with LiOH to the target carboxylic acid (1,2).

参考文献中间体

合成目标

【1】 Chen, J-H.; Michellys, P-Y.; Ardecky, R.J.; Tyhonas, J.S.; Leibowitz, M.D.; Liu, S.; Rungta, D.; D'Arrigo, J.; Mais, D.E.; Miller, A.; Grese, T.A.; Mapes, C.M.; Thompson, A.W.; Boehm, M.F.; Ogilvie, K.M.; Karanewsky, D.S.; RXR modulators. Design and synthesis of new RXR-selective phenyl- and pyridine-locked dienoic acids for the treatment of type 2 diabetes. 225th ACS Natl Meet (March 23 2003, New Orleans) 2003, Abst MEDI 262.
【2】 Jones, T.K.; Ardecky, R.J.; Boehm, M.F.; Hamann, L.G.; Thompson, A.J.; Michellys, P.-Y.; Tyhonas, J.S.; Faulkner, A.L.; Mapes, C.M.; Chen, J.-H. (Ligand Pharmaceuticals, Inc.); RXR modulators with improved pharmacologic profile. EP 1216221; WO 0119770 .

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)	63974	2,4-di(tert-butyl)-6-iodophenol		C₁₄H₂₁IO	详情	详情
(II)	63975	1,5-di(tert-butyl)-3-iodo-2-propoxybenzene; 2,4-di(tert-butyl)-6-iodophenyl propyl ether		C₁₇H₂₇IO	详情	详情
(III)	45993	2-formylphenylboronic acid	40138-16-7	C₇H₇BO₃	详情	详情
(IV)	63976	3',5'-di(tert-butyl)-2'-propoxy[1,1'-biphenyl]-2-carbaldehyde		C₂₄H₃₂O₂	详情	详情
(V)	44704	ethyl (E)-4-(diethoxyphosphoryl)-3-methyl-2-butenoate	41891-54-7	C₁₁H₂₁O₅P	详情	详情
(VI)	63977	ethyl (2E,4E)-5-[3',5'-di(tert-butyl)-2'-propoxy[1,1'-biphenyl]-2-yl]-3-methyl-2,4-pentadienoate		C₃₁H₄₂O₃	详情	详情

Extended Information