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【结 构 式】

【分子编号】41198

【品名】5,6-bis(4-fluoroanilino)-2-benzofuran-1,3-dione

【CA登记号】

【 分 子 式 】C20H12F2N2O3

【 分 子 量 】366.3237664

【元素组成】C 65.58% H 3.3% F 10.37% N 7.65% O 13.1%

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:(VII)

The silylation of butane-2,3-dione(I) with TMSCl and TEA in hot DMF gives the silylated enol (II), which is cyclized with dimethyl acetylenedicarboxylate (III) in refluxing toluene to yield 4,5-bis(trimethylsilyloxy)-3,6-dihydrophthalic acid dimethyl ester (IV). The condensation of (IV) with 4-fluoroaniline (V), with simultaneous aromatization in refluxing acetic acid affords 4,5-bis(4-fluorophenylamino)phthalic acid dimethyl ester (VI), which is hydrolyzed with LiOH in methanol and anhydrized with acetic anhydride in toluene giving the corresponding phthalic anhydride (VII). Finally this compound is treated with ammonium formate at 140-50 C to furnish the target phthalimide.

1 Traxler, P.; Lydon, N.; Recent advances in protein tyrosine kinase inhibitors. Drugs Fut 1995, 20, 12, 1261.
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) 37053 biacetyl 431-03-8 C4H6O2 详情 详情
(II) 41193 2,2,7,7-tetramethyl-4,5-dimethylene-3,6-dioxa-2,7-disilaoctane; 1-methylene-2-[(trimethylsilyl)oxy]-2-propenyl trimethylsilyl ether C10H22O2Si2 详情 详情
(III) 24551 Dimethyl acetylenedicarboxylate; Dimethyl 2-butynedioate;Acetylenedicarboxylic acid dimethyl ester 762-42-5 C6H6O4 详情 详情
(IV) 41194 dimethyl 4,5-bis[(trimethylsilyl)oxy]-1,4-cyclohexadiene-1,2-dicarboxylate C16H28O6Si2 详情 详情
(V) 37690 4-fluorophenylamine; 4-fluoroaniline 371-40-4 C6H6FN 详情 详情
(VI) 41197 dimethyl 4,5-bis(4-fluoroanilino)phthalate C22H18F2N2O4 详情 详情
(VII) 41198 5,6-bis(4-fluoroanilino)-2-benzofuran-1,3-dione C20H12F2N2O3 详情 详情
Extended Information