177-INDOLE-5-CARBOXYLIC ACID 2- METHYL-, ETHYL ESTER

Indole-2-carboxylic acid, 3-methyl-ethyl ester... 

Indole-2-carboxylic acid, 3-methyl-ethyl ester chlorination, 4, 215 Indolecarboxylic acids decarboxylation, 4, 286 esterification, 4, 287 Indole-2-carboxylic acids esters... 

To a solution of the S-(+)-4-acethoxy-9-[2-(5-ethyl-l,2,3,6-tetrahydro-pyridin-3yl)-l-(lH-indol-2-yl)-l-methoxycarbonyl-ethyl]-3a-ethyl-5-hydroxy-8-methoxy-6-methyl-3a,4,5,5a,6,ll,12,12b-octahydro-lH-6,12a-diaza-indeno[7,l-ca]fluorene-5-carboxylic acid methyl ester in dioxane and glacial acetic acid was added 37% aqueous formaldehyde and the mixture stirred at 35°C for 24 h. The solution was evaporated in vacuo and the residue suspended in chloroform and washed with cold aqueous 5% K2C03 solution. The chloroform layer was dried (MgS04), filtered, and evaporated. The residue was chromatographed eluting with EtOAc/MeOH, 10% NH4OH to give the product navelbine. 

Indole, 1-methyl-, 40, 68 Indole-3-carbonttrile, 43, 58 Indoie-3-carboxaldehyde, conversion to indole-3-carbonitrile, 43, 58 Indole-2-carboxylic acid, ethyl ester, 43, 40... 

C jH2,NOSi) see Indanorex (lS-cii)-2,3-dihydro-l//-indene-l,2-diol (G7H10O2 6752S-22-7) see Indinavir sulfate (laS)-la,6a-dihydro-6//-indenori,2-6]oxirene (CgHjO 67528-26-1) see Indinavir sulfate (2,3-dihydro-l//-inden-4-yl)carbamimidothioic acid methyl ester monohydriodide (C, H 1N2S 40507-77-5) see Indanazoline 23-dibydro-l//-indole-2-carboxylic acid ethyl ester (C iH, N02 50501-07-0) see Perindopril... 

Esters of 2-(2-azidophenyl)ethyl alcohol are photolyzed under a high-pressure mercury lamp to a reactive nitrene intermediate which, following insertion into the alkyl side-chain, undergoes elimination to give the free carboxylic acid (up to 32%) and producing indole. The photochemical release was somewhat improved (65-80%) when 5-azido-4-(hydroxy-methyl)-l-methoxy naphthalene was used (see Scheme 27). 

One route to o-nitrobenzyl ketones is by acylation of carbon nucleophiles by o-nitrophenylacetyl chloride. This reaction has been applied to such nucleophiles as diethyl malonatc[l], methyl acetoacetate[2], Meldrum s acid[3] and enamines[4]. The procedure given below for ethyl indole-2-acetate is a good example of this methodology. Acylation of u-nitrobenzyl anions, as illustrated by the reaction with diethyl oxalate in the classic Reissert procedure for preparing indolc-2-carboxylate esters[5], is another route to o-nitrobenzyl ketones. The o-nitrophenyl enamines generated in the first step of the Leimgruber-Batcho synthesis (see Section 2.1) are also potential substrates for C-acylation[6,7], Deformylation and reduction leads to 2-sub-stituted indoles. 

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