522613-61-2

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 32338-02-6 2-bromo-4-methoxyaniline 
• 18437-68-8 tert-butyl N-(4-methoxyphenyl)carbamate 
• 104-92-7 1-bromo-4-methoxy-benzene 
• 4248-19-5 tert-butyl carbazate 

Downstream Products

• 522613-62-3 (4-methoxy-2-vinylphenyl)carbamic acid tert-butyl ester 
• 1370735-35-5 tert-butyl 2-bromo-4-methoxyphenyl(((chloromethyl)dimethylsilyl)methyl)carbamate 
• 32338-02-6 2-bromo-4-methoxyaniline 

Relevant academic research and scientific papers

Solvent-free, uncatalyzed asymmetric "ene" reactions of: N-Tert-butylsulfinyl-3,3,3-Trifluoroacetaldimines: A general approach to enantiomerically pure α-(trifluoromethyl)tryptamines

A novel approach to regioselectively substituted and stereoselectively α-Trifluoromethylated tryptamines is reported based on the ene reaction of Boc-protected 3-methyleneindolines with optically pure (R)-or (S)-Tert-butanesulfinyltrifluoroacetaldimine. B

Installation of protected ammonia equivalents onto aromatic & heteroaromatic rings in water enabled by micellar catalysis

A single set of conditions consisting of a palladium catalyst, a commercially available ligand, and a base, allow for several types of C-N bond constructions to be conducted in water with the aid of a commercially available "designer" surfactant (TPGS-750-M). Products containing a protected NH2 group in the form of a carbamate, sulfonamide, or urea can be fashioned starting with aryl or heteroaryl bromides, iodides, and in some cases, chlorides, as substrates. Reaction temperatures are in the range of room temperature to, at most, 50 °C, and result in essentially full conversion and good isolated yields.

Palladium-catalyzed annulation of haloanilines and halobenzamides using norbornadiene as an acetylene synthon: A route to functionalized indolines, isoquinolinones, and indoles

A general procedure for the palladium-catalyzed annulation of substituted haloanilines with norbornadiene gives functionalized indolines in 51-98% yield. These indolines can be rapidly converted to benzenoid- substituted indoles and tricyclic indolines. Extension to the use of substituted halobenzamides gives functionalized isoquinolinones in up to 86% yield.

Palladium-catalyzed aryl amination-heck cyclization cascade: A one-flask approach to 3-substituted indoles

(Chemical Equation Presented) Two for the price of one: A Pd/dppf-based catalyst provides access to the title compounds from 1,2-dihalogenated aromatic compounds and allylic amines in a single reaction flask. The initial aryl amination step occurs with excellent selectivity for the aryl iodide to ensure the formation of a single indole regioisomer, which can be functionalized in situ by N-arylation (see scheme). dba = dibenzylideneacetone, dppf = 1,1′-bis(diphenylphospanyl)ferrocene.

Indole synthesis by controlled carbolithiation of o-aminostyrenes

An effective synthesis of the functionalized indole ring system has been developed from substituted o-aminostyrene starting material. Our methodology involves a novel cascade reaction sequence of alkyllithium addition to the styrene double bond and subsequent trapping of the intermediate organolithium with a suitable electrophile, followed by an in situ ring closure and dehydration to generate the indole ring. This new reaction sequence allows for the introduction of molecular diversity at all positions on the indole scaffold. The procedure was shown to be successful with a range of both C and N substituents on the o-aminostyrenes. The reaction sequence was tolerant to the reactivity range of alkyllithiums such as tert-, sec-, and n-butyllithium. The electrophiles used were DMF, which generated indole products with C-2 unsubstituted, and nitriles, which incorporated the nitrile substituent at C-2. The o-aminostyrene starting materials were generated by a Pd-catalyzed cross-coupling reaction of a vinyl boronic acid equivalent with the readily available substituted o-bromoanilines.