58602-02-1

Usage

Preparation

Interestingly, direct nitration of 2-fluoro and 2,6-difluoropyridine with nitronium tetrafluoroborate achieved a degree of success and whilst 2-fluoropyridine gave mostly the N-nitro salt, a 6% yield of 5-nitro-2-fluoropyridine was obtained and 2,6-difluoropyridine gave a 20% yield of 3-nitro-2,6-difluoropyridine.

InChI:InChI=1/C5H2F2N2O2/c6-4-2-1-3(9(10)11)5(7)8-4/h1-2H

Upstream product

• 1513-65-1 2,6-difluoro pyridine 
• 16013-85-7 2,6-dicholoro-3-nitropyridine 
• 7664-93-9 sulfuric acid 

Downstream Products

• 108118-69-0 2,6-difluoropyridin-3-ylamine 
• 179557-98-3 1-Benzyl-4-[N-ethyl-N-(6-fluoro-3-(nitro)-2-pyridinyl)amino]piperidine 
• 181579-38-4 1-Benzyl-4-[N-methyl-N-(3-nitro-6-fluoro-2-pyridinyl)amino]piperidine 

Relevant academic research and scientific papers

PYRIDINYL AND PYRAZINYL-(AZA)INDOLSULFONAMIDES

The present invention relates to pyridinyl and pyrazinyl-(aza)indolsulfonamides having GPR17 modulator activity. The compounds have utility in the treatment of a variety of GPR17-associated disorders.

Facile preparation of 3-substituted-2,6-difluoropyridines: Application to the synthesis of 2,3,6-trisubstituted pyridines

We report a facile method for the difluorination of 3-substituted-2,6-dichloropyridines using cesium fluoride as a fluorination reagent in dimethyl sulfoxide. It is proposed that this method for preparing 3-substituted-2,6-difluoropyridines is simpler and easier than those reported in previous literature. To examine the utility of 3-substituted-2,6-difluoropyridines in synthetic chemistry, we also demonstrate a subsequent conversion to 2,3,6-trisubstituted pyridines by a tandem nucleophilic aromatic substitution.

POLYCYCLIC COMPOUND

Disclosed is a compound represented by the formula (I): or a pharmacologically acceptable salt thereof, which is effective as a therapeutic or prophylactic agent for a disease induced by Aβ, wherein Ar1 represents an imidazolyl group which may be substituted with a C1-6 alkyl group, or the like; Ar2 represents a phenyl group which may be substituted with a C1-6 alkoxy group, or the like; X1 represents a double bond, or the like; and Het represents a triazolyl group or the like which may be substituted with a C1-6 alkyl group or the like, or the like.

Electrophilic tetraalkylammonium nitrate nitration. II. Improved anhydrous aromatic and heteroaromatic mononitration with tetramethylammonium nitrate and triflic anhydride, including selected microwave examples

A new one-pot nitration employing tetramethylammonium nitrate and trifluoromethanesulfonic anhydride in dichloromethane to provide a ready source of the nitronium triflate nitrating agent is presented. Rapid and selective nitration with a variety of aromatic and heteroaromatic substrates is achieved resulting in the synthesis of several novel organic compounds. A distinct advantage is the removal of undesired byproducts by aqueous workup. This very mild nitration permits large-scale syntheses and gives high isolated product yields that often require no further purification. This tetramethylammonium nitrate-based nitration also has been applied to microwave-assisted conditions, and the results with several compounds are outlined.

Non-nucleoside reverse transcriptase inhibitors

Provided are compounds of the general formula I: wherein R2 is selected from the group consisting of H, F, Cl, (C1-4) alkyl, (C3-4) cycloalkyl and CF3; R4 is H or Me; R5 is H, Me or Et, wit

Selective fluorination by halogen exchange of chlorodiazines and chloropyridines promoted by the 'proton sponge' - Triethylamine tris(hydrogen fluoride) system

The 'proton sponge' - triethylamine tris(hydrogen fluoride) mixtures provide a mild and efficient fluorinating reagent to introduce selectively fluorine atoms by halogen exchange into chlorodiazines and chloronitropyridine series.

SYNTHESIS OF SOME 1-ALKYL-1,4-DIHYDRO-4-OXO-1,7-NAPHTHYRIDINE-3-CARBOXYLIC ACIDS

Reaction of substituted 2-aminopyridines IIIa, IIIb, IIIe, and IIIf with ethyl ethoxymethylene malonate provided corresponding pyridylaminomethylenemalonates Va-Vd, respectively.Thermal cyclization of Va, Vc, and Vd yielded substituted ethyl 4-hydroxy-1,7-naphthyridine-3-carboxylates VIa, VIc, and VId.Compounds VIc and VId treated with morpholine have 8-morpholino derivatives VIe and VIf.These compounds were ethylated to mixtures of N-ethylated (VIIa, VIIb) and O-ethylated products (VIIIa, VIIIb).Compound VIIIb was also prepared from ethyl 4-chloro-6-fluoro-8-morpholino-1,7-naphthyridine-3-carboxylate VIIIc and sodium ethanolate.Esters VIIa and VIIb were hydrolyzed under acidic conditions to the respective acids VIIc and VIId.

Aprotic Nitration (NO2+BF4-) of 2-Halo- and 2,6-Dihalopyridines and Transfer-Nitration Chemistry of Their N-Nitropyridinium Cations

NO2+BF4- nitration of 2,6-dibromo-1 and 2,6-dichloropyridine 2 in CH3CN results in predominant C-nitration, whereas in CH2Cl2, N-nitration is predominant.With 2,6-difluoropyridine 3 only C-nitration was observed.Dehalogenation of the C-nitrated 1 and 2 affords 3-nitropyridine (3-NP) in moderate but greatly improved yields over conventional protic nitration of pyridine.Despite favorable presence of steric inhibition to resonance and the I-effect of halogens, N-nitrated pyridinium salts 1b and 2b do not transfer-nitrate to aromatics even under forcing conditions.The lack of transfer-nitration reactivity is not due to in situ rearrangement of the nitro onium to nitrito oniums ions.A mechanism involving neighboring group participation by the 2,6-halogens is proposed.The monohalo-N-nitropyridinium cations transfer-nitrate toluene and benzene.Transfer nitration selectivity of the 2-bromo-N-nitro- and 2-chloro-N-nitropyridinium cations are comparable (KT/KB = 41-44), but the 2-fluoro-N-nitro cation is much less selective (more reactive) (KT/KB = 15.4), indicative of a stronger -I effect, weakening the N+-N+ bond.

Imidazo pyridine-2-ones and pharmaceutical compositions and methods of treatment utilizing same

1,3-Dihydroimidazo[4,5-b]pyridin-2-ones and corresponding thiones have utility as analgesic, antipyretic and antiinflammatory agents. They are generally prepared by treatment of a 2,3-diaminopyridine with phosgene or thiosphosgene followed by further substitution if desired.