2-bromo-1-(4-bromophenyl)-1-ethanone -Drug Synthesis Database

【结构式】

【分子编号】39243

【品名】2-bromo-1-(4-bromophenyl)-1-ethanone

【CA登记号】99-73-0

【分子式】C₈H₆Br₂O

【分子量】277.94304

【元素组成】C 34.57% H 2.18% Br 57.5% O 5.76%

与该中间体有关的原料药合成路线共 2 条

合成路线1 合成路线2

合成路线1

该中间体在本合成路线中的序号：(I)

Condensation of 4-bromophenacyl bromide (I) with phenol in the presence of potassium carbonate produced phenoxyacetophenone (II), which was cyclized to benzofuran (III) upon treatment with polyphosphoric acid in refluxing xylene. Suzuki coupling of (III) with 4-methoxybenzeneboronic acid (IV) gave the biphenyl benzofuran (V). The phenolic derivative (VI) was prepared by demethylation of ether (V) with boron tribromide. Lithiation of (VI) with n-butyllithium, followed by addition of N-methoxy-N-methyl benzamide afforded ketone (VII), which was converted to the benzyl benzofuran (VIII) by means of a modified Wolff-Kishner reduction. Coupling of (VIII) with methyl (S)-3-phenyllactate (IX) under Mitsunobu conditions furnished the corresponding ether (X). The methyl ester group of (X) was finally hydrolyzed with NaOH to yield the title carboxylic acid.

参考文献中间体

合成目标

【1】 Malamas, M.S.; Sredy, J.; Moxham, C.; et al.; Novel benzofuran and benzothiophene biphenyls as inhibitors of protein tyrosine phosphatase 1B with antihyperglycemic properties. J Med Chem 2000, 43, 7, 1293.
【2】 McDevitt, R.E.; Malamas, M.S.; Adebayo, F.O. (American Home Products Corp.); Biphenyl oxo-acetic acids useful in the treatment of insulin resistance and hyperglycemia. WO 9958518 .

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)	39243	2-bromo-1-(4-bromophenyl)-1-ethanone	99-73-0	C₈H₆Br₂O	详情	详情
(II)	39244	1-(4-bromophenyl)-2-phenoxy-1-ethanone		C₁₄H₁₁BrO₂	详情	详情
(III)	39245	3-(4-bromophenyl)-1-benzofuran		C₁₄H₉BrO	详情	详情
(IV)	39246	4-methoxyphenylboronic acid	5720-07-0	C₇H₉BO₃	详情	详情
(V)	39247	4'-(1-benzofuran-3-yl)[1,1'-biphenyl]-4-yl methyl ether; 3-(4'-methoxy[1,1'-biphenyl]-4-yl)-1-benzofuran		C₂₁H₁₆O₂	详情	详情
(VI)	39248	4'-(1-benzofuran-3-yl)[1,1'-biphenyl]-4-ol		C₂₀H₁₄O₂	详情	详情
(VII)	39249	[3-(4'-hydroxy[1,1'-biphenyl]-4-yl)-1-benzofuran-2-yl](phenyl)methanone		C₂₇H₁₈O₃	详情	详情
(VIII)	39250	4'-(2-benzyl-1-benzofuran-3-yl)[1,1'-biphenyl]-4-ol		C₂₇H₂₀O₂	详情	详情
(IX)	39252	methyl (2S)-2-hydroxy-3-phenylpropanoate		C₁₀H₁₂O₃	详情	详情
(X)	39251	methyl (2S)-2-[[4'-(2-benzyl-1-benzofuran-3-yl)[1,1'-biphenyl]-4-yl]oxy]-3-phenylpropanoate		C₃₇H₃₀O₄	详情	详情

合成路线2

该中间体在本合成路线中的序号：(I)

参考文献中间体

合成目标

【1】 Kim DY, Kim JG, Cho DJ, et aL. 2005. Method for preparing 3-phenyl-4-[ (4-methylsulfonyl) phenyl]-2(5H)-furanone as a cyclooxygenase-2 inhibitor. W0 2005051935(奉专利属于Yang Pharm Co, Ltd,S Korea)．

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)	39243	2-bromo-1-(4-bromophenyl)-1-ethanone	99-73-0	C₈H₆Br₂O	详情	详情
(II)	16148	Benzeneacetic acid; 2-Phenylacetic acid; Phenyl Acetic Acid	103-82-2	C₈H₈O₂	详情	详情
(III)	66649	1-(4-bromophenyl)-2-(2-oxo-2-phenylethoxy)ethanone		C₁₆H₁₃BrO₃	详情	详情
(IV)	66650	4-(4-bromophenyl)-3-phenylfuran-2(5H)-one		C₁₆H₁₁BrO₂	详情	详情

Extended Information