1-bromo-4-isobutylbenzene -Drug Synthesis Database

【结构式】

【分子编号】26894

【品名】1-bromo-4-isobutylbenzene

【CA登记号】2051-99-2

【分子式】C₁₀H₁₃Br

【分子量】213.11722

【元素组成】C 56.36% H 6.15% Br 37.49%

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：(V)

Reaction of 1-bromo-4-isobutylbenzene (V) with magnesium generated the corresponding Grignard reagent (VI), which was condensed with trimethyl borate to afford, after acid hydrolysis, arylboronic acid (VII). This was nitrated with acetyl nitrate to produce nitro derivative (VIII). Subsequent reduction of the nitro group of (VIII) by hydrogenation over Pd/C gave 2-amino-4-isobutylphenyl boronic acid (IX). Suzuki coupling of boronic acid (IX) with bromosulfonamide (IV) produced the required biphenyl (X). The methoxyethoxymethyl group was finally deprotected by treatment with HCl to furnish the title compound.

参考文献中间体

合成目标

【1】 Murugesan, N.; Hunt, J.T. (Bristol-Myers Squibb Co.); Phenyl sulfonamide and their use as endothelin antagonists. EP 0569193; JP 1994049046; US 5514696 .

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(IV)	26893	2-bromo-N-(3,4-dimethyl-5-isoxazolyl)-N-[(2-methoxyethoxy)methyl]benzenesulfonamide		C₁₅H₁₉BrN₂O₅S	详情	详情
(V)	26894	1-bromo-4-isobutylbenzene	2051-99-2	C₁₀H₁₃Br	详情	详情
(VI)	26895	bromo(4-isobutylphenyl)magnesium		C₁₀H₁₃BrMg	详情	详情
(VII)	26896	4-isobutylphenylboronic acid		C₁₀H₁₅BO₂	详情	详情
(VIII)	26897	4-isobutyl-2-nitrophenylboronic acid		C₁₀H₁₄BNO₄	详情	详情
(IX)	26898	2-amino-4-isobutylphenylboronic acid		C₁₀H₁₆BNO₂	详情	详情
(X)	26899	2'-amino-N-(3,4-dimethyl-5-isoxazolyl)-4'-isobutyl-N-[(2-methoxyethoxy)methyl][1,1'-biphenyl]-2-sulfonamide		C₂₅H₃₃N₃O₅S	详情	详情

Extended Information