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【结 构 式】 
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【分子编号】39759 【品名】3-chlorophenylboronic acid 【CA登记号】63503-60-6 |
【 分 子 式 】C6H6BClO2 【 分 子 量 】156.37614 【元素组成】C 46.09% H 3.87% B 6.91% Cl 22.67% O 20.46% |
合成路线1
该中间体在本合成路线中的序号：(V)Bromination of ethyl 4-hydroxybenzoate (I) by means of N-bromosuccinimide and HBF4.Et2O produced ethyl 3-bromo-4-hydroxybenzoate (II), which was further iodinated to (III) employing I2 and K2CO3. Subsequent condensation of (III) with ethylene glycol under Mitsunobu conditions afforded (hydroxyethyl)ether (IV). Palladium-catalyzed coupling of (IV) with 3-chlorophenylboronic acid (V) gave rise to terphenyl derivative (VI). Amide (VII) was then obtained by treatment of ester (VI) with n-dodecylamine in the presence of butyllithium. Finally, alcohol (VII) oxidation using N-methylmorpholine-N-oxide and tetrapropylammonium perruthenate furnished the title carboxylic acid.
| 【1】 Butera, J.A.; Caufield, C.E.; Greenfield, A.; Gundersen, E.G.; Lennox, J.R.; Graceffa, R.F.; Mayer, S.C.; Katz, A.H.; McDevitt, R.E.; Havran, L.M. (American Home Products Corp.); 2,3,5-Substd. biphenyls useful in the treatment of insulin resistance and hyperglycemia. WO 9961410 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| 40735 | 1-dodecanamine; dodecylamine | 124-22-1 | C12H27N | 详情 | 详情 | |
| (I) | 13492 | ethyl p-hydroxybenzoate; ethyl 4-hydroxybenzoate | 120-47-8 | C9H10O3 | 详情 | 详情 |
| (II) | 39756 | ethyl 3-bromo-4-hydroxybenzoate | C9H9BrO3 | 详情 | 详情 | |
| (III) | 39757 | ethyl 3-bromo-4-hydroxy-5-iodobenzoate | C9H8BrIO3 | 详情 | 详情 | |
| (IV) | 39758 | ethyl 3-bromo-4-(2-hydroxyethoxy)-5-iodobenzoate | C11H12BrIO4 | 详情 | 详情 | |
| (V) | 39759 | 3-chlorophenylboronic acid | 63503-60-6 | C6H6BClO2 | 详情 | 详情 |
| (VI) | 39760 | C23H20Cl2O4 | 详情 | 详情 | ||
| (VII) | 39761 | C33H41Cl2NO3 | 详情 | 详情 |
合成路线2
该中间体在本合成路线中的序号：(III)Bromination of 3-cyano-6-methyl-2-pyridone (I) by means of N bromosuccinimide (NBS) in 1,2-dichloroethane affords the 5-bromopyridone (II). Subsequent Suzuki coupling of (II) with 3-chlorophenylboronic acid (III) yields the 5-phenylpyridone (IV). Radical bromination of (IV) with NBS and AIBN produces the bromomethyl derivative (V). This is then converted to alcohol (VI) upon refluxing in aqueous dioxane in the presence of celite
| 【1】 Hasvold, L.A.; et al.; Design and synthesis of pyridone farnesyltransferase inhibitors. 224th ACS Natl Meet (Aug 18 2002, Boston) 2002, Abst MEDI 126. |
| 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) | 27560 | 6-methyl-2-oxo-1,2-dihydro-3-pyridinecarbonitrile | 4241-27-4 | C7H6N2O | 详情 | 详情 |
| (II) | 60859 | 5-bromo-6-methyl-2-oxo-1,2-dihydro-3-pyridinecarbonitrile | C7H5BrN2O | 详情 | 详情 | |
| (III) | 39759 | 3-chlorophenylboronic acid | 63503-60-6 | C6H6BClO2 | 详情 | 详情 |
| (IV) | 60860 | 5-(3-chlorophenyl)-6-methyl-2-oxo-1,2-dihydro-3-pyridinecarbonitrile | C13H9ClN2O | 详情 | 详情 | |
| (V) | 60861 | 6-(bromomethyl)-5-(3-chlorophenyl)-2-oxo-1,2-dihydro-3-pyridinecarbonitrile | C13H8BrClN2O | 详情 | 详情 | |
| (VI) | 60862 | 5-(3-chlorophenyl)-6-(hydroxymethyl)-2-oxo-1,2-dihydro-3-pyridinecarbonitrile | C13H9ClN2O2 | 详情 | 详情 |