698379-26-9

Upstream product

• 108-88-3 toluene 
• 698378-63-1 ethyl α,α-difluoro-α-(phenylseleno)acetate 
• 625-95-6 3-Iodotoluene 
• 667-27-6 Ethyl bromodifluoroacetate 
• 108-44-1 1-amino-3-methylbenzene 
• 205865-67-4 α-(trimethylsilyl)difluoroacetic acid ethyl ester 
• 32578-31-7 3-tolyl triflate 

Relevant academic research and scientific papers

Synthetic method of aromatic ring group or aromatic heterocyclic tetrazole

The synthetic method comprises the following steps: (1) reacting 1.0 eq of ArI or HArI with 1.2 eq of ethyl 2, 2-difluoroacetate in the presence of DMSO as a solvent and 4.0 eq of Cu under the protection of nitrogen at 30 DEG C and 50 DEG C, and purifying to obtain a first intermediate compound; (2) dissolving 1.0 eq of the first intermediate compound in a mixed solvent of THF and water, adding 2.0 eq of LiOH, reacting at room temperature for 2 hours, spin-drying the solvent, adding HCl until the pH value is equal to 3, and filtering to obtain a second intermediate compound; and (3) reacting 1.0 eq of the second intermediate compound with 2.0 eq of diphenyl azide phosphate in the presence of 2.5 eq of triethylamine by taking tert-butyl alcohol as a solvent to generate aromatic ring group or aromatic heterocyclic tetrazole. The invention provides a novel synthetic method of aromatic ring group or aromatic heterocyclic tetrazole, wherein a target compound can be more conveniently obtained, and reagents participating in the reaction are low in toxicity, mild in reaction condition, simple and safe in aftertreatment, good in product quality and suitable for large-scale production.

Palladium-Catalyzed Cross-Coupling of Ethyl Bromodifluoroacetate with Aryl Bromides or Triflates and Cross-Coupling of Ethyl Bromofluoroacetate with Aryl Iodides

A palladium-catalyzed Negishi cross-coupling reaction of ethyl bromodifluoroacetate with aryl bromides or aryl triflates to construct C(sp2)-CF2 bonds is described. The reaction was conducted under mild reaction conditions, and no preparation of organozinc reagents is required. This is the first report encompassing the conversion of aryl triflates into products containing C-CF2 bonds. In addition, the construction of C(sp2)-CHF bonds was achieved under mild conditions via a cross-coupling of aryl iodides with ethyl bromofluoroacetate.

Silver-Mediated C–H Difluoromethylation of Arenes

The first AgI-mediated C–H ethoxycarbonyl difluoromethylation with TMSCF2COOEt (TMS = trimethylsilyl) has been developed. The radical difluoromethylation proceeds smoothly to give the difluoromethylated arenes in moderate to high yie

Easy Access to Difluoromethylene-Containing Arene Analogues through Palladium-Catalysed C–H Olefination

An efficient palladium-catalysed ortho-C–H olefination of α,α-difluorophenylacetic acid derivatives using 8-aminoquinoline as a bidentate directing group has been developed. A range of olefinated arenes can thus be synthesized in a concise way. This reaction provides an easy and straightforward route to a panel of difluoromethylated arene analogues in moderate to good yields, with a satisfactory tolerance of common functional groups. Transformation of the products into a variety of other difluoromethylene-containing compounds demonstrates the utility of this method.

3-(Fluorovinyl)pyrazoles and their use

The present application relates to novel 3-(fluorovinyl)pyrazole derivatives, to processes for their preparation, to their use for treatment and/or prevention of diseases and to their use for the preparation of medicaments for treatment and/or prevention of diseases, in particular for treatment and/or prevention of hyperproliferative and angiogenic diseases and those diseases which arise from metabolic adaptation to hypoxic states. Such treatments can be carried out as monotherapy or also in combination with other medicaments or further therapeutic measures.

The asymmetric synthesis of CF3- or -CF2-substituted tetrahydroquinolines by employing a chiral phosphoric acid as catalyst

CF3- or -CF2-containing tetrahydroquinolines have been asymmetrically synthesized from the reaction of fluorinated N-arylimines with benzyl N-vinylcarbamate in the presence of a chiral phosphoric acid.

DERIVATIVES OF 4-(2-AMINO-1-HYDROXYETHYL)PHENOL AS AGONISTS OF THE β2 ADRENERGIC RECEPTOR

The present invention provides a compound of formula (I) wherein: R1 is a group selected from -CH2OH, -NHC(O)H and R2 is a hydrogen atom; or R1 together with R2 form the group -NH-C(O)-CH=CH- wherein the nitrogen atom is bound to the carbon atom in the phenyl ring holding R1 and the carbon atom is bound to the carbon atom in the phenyl ring holding R2; R3 is selected from hydrogen and halogen atoms or groups selected from -SO-R5, -SO2- R5, -NH-CO-NH2, -CO-NH2, hydantoino, C1-4alkyl, C1-4alkoxy and -SO2NR5R6; R4 is selected from hydrogen atoms, halogen atoms and C1-4alkyl groups; R5 is a C1-4alkyl group or C3-8 cycloalkyl; R6 is independently selected from hydrogen atoms and C1-4alkyl groups; n, p and q are independently 0, 1 , 2, 3 or 4; m and s are independently 0, 1 , 2 or 3; r is 0, 1 or 2; with the provisos that: at least one of m and r is not 0; the sum n+m+p+q+r+s is 7, 8, 9, 10, 11 , 12 or 13; the sum q+r+s is 2, 3, 4, 5 or 6 or a pharmaceutically-acceptable salt, solvate or stereoisomer thereof.

Aromatic substitution with photochemically generated difluoromethyl radicals bearing electron-withdrawing group

Novel and facile aromatic and heteroaromatic substitutions with difluoromethyl radicals bearing electron-withdrawing group generated by the photo-initiated Se-CF2 bond cleavage of ethyl α,α- difluoro-α-(phenylseleno)acetate and diethyl α,α- difluoromethyl-α-(phenylseleno)phosphonate were successfully carried out to provide the corresponding α-aryl-α,α-difluoroacetates and a-aryl-α,α-difluoromethylphosphonates in good to moderate yields.