Indoles Experimental Procedure

Experimental Procedure 4.2.2. Preparation of an Indole by Intramolecular C-H Insertion Methyl (2S)-2-(3-Acetyl-2-hydroxy-5-aito-lff-l-indolyl)-3-phenylpropanoate [1083]... 

Experimental Procedure 4.2.3. Alkylation of Indole by Intermolecular C-H Insertion 3-( l//-3-Indolyl)-2,4-pyrrolidinedione... 

Carbenoid addition of diazocarbonyl compounds to pyrrole, A -alkylpyrroles, indole, N-alkylindoles, imidazole, and benzimidazole does not result in cyclopropanation, but leads to the formal products of carbene insertion into a heterocyclic C-H bond (see Houben-Weyl, Vol.E19b, ppll58 and 1334). However, Af-acylpyrroles, and Af-acylindoles - " have successfully been converted into 2-azabicyclo[3.1.0]hex-3-ene-exo-6-carboxylates and alkyl-1,la,2,6b-tetrahydrocyclopropa[ ]indole-exo-l-carboxylate, respectively (for an experimental procedure, see Houben-Weyl, Vol.E19b, pll60). 

Progress has been made in the experimental procedures for the formylation of pyrazoles (Vilsmeir-Haack reaction) at their 4 position <93JHC957, 94CPB237). For instance, 4/f-pyrazolo[l,5-a]indoles are formylated under milder eonditions than pyrazoles <94CPB237>. 

R. J. Sundberg, Indoles (1996), Academic Press, London. An excellent review covering the gamut of methods, including selective experimental procedures. 

Several outstanding books on name reactions in organic chemistry are available. These typically briefly cover the classic indole name reactions with examples, references, and, in some cases, experimental procedures. 

The CH-activation can be combined with an intramolecular carbopalladation reaction to yield cyclic aromatic systems. In this case, indoles can be synthesized in an efficient manner (Experimental Procedure below). ... 

Typical experimental procedure for (S)-3-(l,3-dioxo-l,3-dihy-dro-isoindol-2-yl)-3-fluoro-2-oxo-piperidin-l-carboxylic acid tert-butyl ester (precursor of 3S-fluorothalidomide) using the dihydroquinine/NFSI combination with TMEDA Lithium bis (trimethylsilyl)amide solution l.OM in THF (0.087mL, 0.087 mmol) was added to the solution of 3-(l,3-dioxo-l,3-dihydro-iso-indol-2-yl)-2-oxo-piperidin-l-carboxylic acid tert-hutyl ester (20 mg, 0.058 mmol) and tetramethylethylenediamine (0.013 mL, 0.087 mmol) in THF (l.OmL) at -80°C under Ar. After being stirred for 0.5 hours, the suspension of the dihydroquinine/NFSI combination [the solution of dihydroquinine (28.4 mg, 0.087 mmol) and N-fluorobenzenesulfonimide (27.4 mg, 0.087 mmol) in THF (2.0 mL) was stirred for 1 hour at room temperature under Ar] was dropwise and then stirred for overnight at -80 °C. The reaction was quenched with IN hydrochloric acid, extracted with ethyl acetate, washed with brine, dried over Na2S04 and concentrated under reduced pressure. The residue was purified by silica-... 

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