methyl 3-{[1-(methoxymethyl)-1H-indol-3-yl]carbonyl}-4-quinolinecarboxylate -Drug Synthesis Database

【结构式】

【分子编号】56963

【品名】methyl 3-{[1-(methoxymethyl)-1H-indol-3-yl]carbonyl}-4-quinolinecarboxylate

【CA登记号】

【分子式】C₂₂H₁₈N₂O₄

【分子量】374.396

【元素组成】C 70.58% H 4.85% N 7.48% O 17.09%

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：(VI)

The methanolysis of anhydride (I) with dry refluxing methanol gives the monoester (II), which is treated with COCl2 to yield the acyl chloride (III). The condensation of (III) with indole (IV) by means of ZnCl2/MeMgCl and AlCl3 affords the adduct (V), which is N protected by means of Mom-Cl and NaH in THF to provide the intermediate (VI). The cyclization of (VI) by means of Temda and LiHMDS in THF gives the tetracyclic quinone (VII), which is finally deprotected with hot aq. HCl to provide the target Calothrixin B.

参考文献中间体

合成目标

【1】 Bernardo, P.H.; et al.; A simple and concise route to calothrixin B. Tetrahedron Lett 2002, 43, 16, 2939.

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)	56959	furo[3,4-c]quinoline-1,3-dione		C₁₁H₅NO₃	详情	详情
(II)	56960	4-(methoxycarbonyl)-3-quinolinecarboxylic acid		C₁₂H₉NO₄	详情	详情
(III)	56961	methyl 3-(chlorocarbonyl)-4-quinolinecarboxylate		C₁₂H₈ClNO₃	详情	详情
(IV)	15292	Indole; 1H-indole	120-72-9	C₈H₇N	详情	详情
(V)	56962	methyl 3-(1H-indol-3-ylcarbonyl)-4-quinolinecarboxylate		C₂₀H₁₄N₂O₃	详情	详情
(VI)	56963	methyl 3-{[1-(methoxymethyl)-1H-indol-3-yl]carbonyl}-4-quinolinecarboxylate		C₂₂H₁₈N₂O₄	详情	详情
(VII)	46800	12-(methoxymethyl)-7H-indolo[3,2-j]phenanthridine-7,13(12H)-dione		C₂₁H₁₄N₂O₃	详情	详情

Extended Information