Traceless linking of indoles: General methodology and application to solid phase supported Mannich and Stille reactions

Synlett

Volumn , Issue 1, 2000, Pages 125-127

  Kraxner, Johannes ^a   Arlt, Michael ^b   Gmeiner, Peter ^a  

^a UNIVERSITY OF ERLANGEN NUREMBERG   (Germany)

^b MERCK KGAA   (Germany)

Author keywords

Diethoxymethyl protection; Indoles; Solid phase synthesis; Stille reaction; Traceless linker

Indexed keywords

INDOLE DERIVATIVE;

ACETYLATION; ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; ORGANIC CHEMISTRY; REACTION ANALYSIS; SOLID PHASE EXTRACTION;

EID: 0033964548     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

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16. Experimental details for the preparation of the DEM protected indole 2a: A solution of 1a (889 mg, 6.3 mmol) in triethyl orthoformate (10 ml, 63 mmol) was stirred at 160°C for 24 h. The mixture was concentrated and the residue was purified by flash chromatography (230-400 mesh silica gel, petroleum ether / EtOAc 4:1) to give 2a (1.390 g, 91%).
17. 2O and dried in vacuo to give 598 mg of resin 4a.
18. Starting from 2c, we observed decomposition besides removal of the DEM group. We think that this is due to the more electron rich aromatic system combined with the unsubstituted positions 2 and 3. For 5-bromindole, we observed properties which were similar to those of indole.
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