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【结 构 式】

【分子编号】58335

【品名】methyl 2-amino-5-bromobenzoate

【CA登记号】

【 分 子 式 】C8H8BrNO2

【 分 子 量 】230.06106

【元素组成】C 41.77% H 3.5% Br 34.73% N 6.09% O 13.91%

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)

Addition of methylmagnesium bromide to methyl 2-amino-5-bromobenzoate (I) provides the tertiary alcohol (II). Subsequent ring closure of the amino carbinol (II) with acetaldehyde leads to the benzoxazine (III). Treatment of the bromobenzoxazine (III) with bis(pinacolato)diboron (IV) and [1,1'-bis(diphenylphosphino)ferrocene]palladium(II) chloride furnishes the aryl borate (V). This is finally subjected to Suzuki coupling with 5-bromo-2-thiophenecarbonitrile (VI) to produce the title benzoxazinyl thiophene derivative.

1 Zhang, P.; et al.; Potent nonsteroidal progesterone receptor agonists: Synthesis and SAR study of 6-aryl benzoxazines. Bioorg Med Chem Lett 2002, 12, 5, 787.
2 Jones, T.K.; Zhi, L.; Tegley, C.M.; Fensome, A.; Zhang, P.; Terefenko, E.A.; Marschke, K.B. (Ligand Pharmaceuticals, Inc.; Wyeth); Quinazolinone and benzoxazine derivs. as progesterone receptor modulators. EP 1175404; WO 0066560 .
3 Jones, T.K.; Zhi, L.; Tegley, C.M.; Marschke, K.B.; Grubb, G.S. (Ligand Pharmaceuticals, Inc.; Wyeth); Contraceptive compsns. containing quinazolinone and benzoxazine derivs.. WO 0066164; WO 0066165 .
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) 58335 methyl 2-amino-5-bromobenzoate C8H8BrNO2 详情 详情
(II) 58336 2-(2-amino-5-bromophenyl)-2-propanol C9H12BrNO 详情 详情
(III) 58337 6-bromo-2,4,4-trimethyl-1,4-dihydro-2H-3,1-benzoxazine C11H14BrNO 详情 详情
(IV) 53342 4,4,4',4',5,5,5',5'-Octamethyl-2,2'-bi-1,3,2-dioxaborolane; Bis(pinacolato)diboron; Diboron pinacol ester 73183-34-3 C12H24B2O4 详情 详情
(V) 58338 2,4,4-trimethyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,4-dihydro-2H-3,1-benzoxazine C17H26BNO3 详情 详情
(VI) 58339 4-bromo-2-thiophenecarbonitrile C5H2BrNS 详情 详情
Extended Information