2356-16-3

Usage

Uses

Used in Organic Chemistry:
Triethyl 2-fluoro-2-phosphonoacetate is used as a reactant for Diels-Alder reactions, which are important in the synthesis of complex organic compounds. It is also utilized in the biosynthesis of terpenes, a large and diverse class of organic compounds produced by a variety of organisms.
Used in Stereoselective Synthesis:
Triethyl 2-fluoro-2-phosphonoacetate is used as a reactant for the stereoselective synthesis of unsaturated esters, fluorides, and nitriles from the reactions of aldehydes and ketones using Wadsworth-Emmons phosphonates. This application is crucial in the development of enantiomerically pure compounds, which are essential in the pharmaceutical industry.
Used in Synthesis of Quinolones:
Triethyl 2-fluoro-2-phosphonoacetate is employed as a reactant in the synthesis of quinolones, a class of antibacterial agents that are widely used in the treatment of various bacterial infections.
Used in Horner-Wadsworth-Emmons Asymmetric Hydration:
Triethyl 2-fluoro-2-phosphonoacetate is used as a reactant in the Horner-Wadsworth-Emmons asymmetric hydration, a reaction that allows for the formation of chiral phosphonates, which are valuable intermediates in the synthesis of biologically active molecules.
Used in Addition Reactions and Click Chemistry:
Triethyl 2-fluoro-2-phosphonoacetate is used in addition reactions, which are then applied to click chemistry, a set of powerful and versatile reactions that allow for the rapid and efficient assembly of complex molecules from smaller units.
Used in Asymmetric Intermolecular Stetter Reactions:
Triethyl 2-fluoro-2-phosphonoacetate is used as a reactant in asymmetric intermolecular Stetter reactions, which are important for the synthesis of biologically active molecules with high enantioselectivity.

Synthesis Reference(s)

The Journal of Organic Chemistry, 60, p. 4730, 1995 DOI: 10.1021/jo00120a014

InChI:InChI=1/C8H16FO5P/c1-4-12-8(10)7(9)15(11,13-5-2)14-6-3/h7H,4-6H2,1-3H3/t7-/m1/s1

Upstream product

• 401-56-9 ethyl chlorofluoroacetate 
• 762-04-9 phosphonic acid diethyl ester 
• 7071-02-5 Potassium; (Z)-2-(diethoxy-phosphoryl)-1,2-bis-ethoxycarbonyl-ethenolate 
• 401-55-8 ethyl bromofluoroacetate 
• 122-52-1 triethyl phosphite 
• 867-13-0 diethoxyphosphoryl-acetic acid ethyl ester 
• 65094-25-9 diethyl dibromofluoromethylphosphonate 
• 541-41-3 chloroformic acid ethyl ester 
• 401-58-1 ethyl 2-fluoro-2-iodoacetate 
• 78-40-0 triethyl phosphate 

Downstream Products

• 20397-58-4 ethyl (E)-2-fluoro-3-phenylacrylate 
• 126275-39-6 ethyl 2,4-difluoro-5-phenyl-2(E),4(E)-pentadienoate 
• 85319-53-5 (2E,4Z,6Z)-2-Fluoro-5-methyl-7-(2,6,6-trimethyl-cyclohex-1-enyl)-hepta-2,4,6-trienoic acid ethyl ester 
• 138737-10-7 (E)-4-(tert-Butyl-dimethyl-silanyloxy)-2-fluoro-5-phenyl-7-(tetrahydro-pyran-2-yloxy)-hept-2-enoic acid ethyl ester 
• 138763-15-2 (E)-6-(tert-Butyl-diphenyl-silanyloxy)-6-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-fluoro-4-(tetrahydro-pyran-2-yloxy)-hex-2-enoic acid ethyl ester 
• 110624-99-2 Fluoro-phosphono-acetic acid ethyl ester; compound with cyclohexylamine 
• 171916-53-3 triethyl 2-fluoro-3-oxo-2-phosphono-3-phenylpropanoate 
• 151629-26-4 (E)-ethyl 2-fluoro-3-(1-trityl-1H-imidazol-4-yl)-prop-2-enoate 
• 30094-32-7 (diethoxy phosphoryl) fluoroacetic acid 
• 459-72-3 ethyl 2-fluoroacetate 
• 2319-83-7 ethyl (2Z,4E)-2-fluoro-3-methyl-5-(2',6',6'-trimethyl-1'-cyclohexenyl)-2,4-pentadienoate 
• 180729-70-8 ethyl (2E,4E)-2-fluoro-3-methyl-5-(2',6',6'-trimethyl-1'-cyclohexenyl)-2,4-pentadienoate 

Relevant academic research and scientific papers

A Convenient Synthesis of Ethyl (Diethoxyphosphoryl)fluoroacetate from Ethyl Fluoroacetate

A new synthesis of ethyl (diethoxyphosphoryl)fluoroacetate starting from ethyl fluoroacetate is described for a mole scale.This synthesis does not require the use of special equipment for fluorine chemistry since no hydrogen fluoride is evolved.

Application of fluorocarbethoxy-substituted phosphonate: A facile entry to substituted 2-fluoro-3-oxoesters

Diethyl(fluorocarbethoxymethyl)phosphonate 1a or diisopropyl(fluorocarbethoxymethyl)phosphonate 1b, prepared from triethyl phosphite or triisopropyl phosphite with ethyl bromofluoroacetate, react with n-butyllithium in THF to give the corresponding phosphonate carbanions [(RO)2P(O)CFCO2Et]-Li+ 2a (R = Et) and 2b (R = i-Pr). Addition of trimethylsilyltrifluoroacetate CF3C(O)OSiMe3 to a THF solution of phosphonate carbanions formed the enolate of ethyl trifluoroacetylfluoroacetate [CF3C(O)CFCO2Et]-Li+ 3. Subsequent protonation, alkylation or allylation of the enolate afforded substituted 2,4,4,4-tetrafluoro-3-oxoesters CF3C(O)CFR1CO2Et 10.

Synthesis of fluorinated phosphonoacetate derivatives of carbocyclic nucleoside monophosphonates and activity as inhibitors of HIV reverse transcriptase

The syntheses of compounds 8-10 are described; the compounds showed some activity as inhibitors of HIV reverse transcriptase (IC50 ≥ 365 μM).

New routes to diethyl 1-fluoromethylphosphonocarboxylates and diethyl 1-fluoromethylphosphonocarboxylic acid

Diethyl 1-fluoromethylphosphonocarboxylic esters 4, bearing a variety of ester groups (alkyl, aryl), have been conveniently prepared in a one-pot process, by reaction of chloroformates with 1-lithio-1-fluoro-1-(trimethylsilyl)methylposphonate 2 derived from 1,1-dibromo-1-fluoromethylphosphonate 1. The overall yields generally range from 80 to 91%. Reaction of 2 with CO2 leads to a novel efficient synthesis of diethyl 1-fluoromethylphosphonocarboxylic acid 7 in 86% yield.

Preparation of triethyl 2-fluoro-2-phosphonoacetate

Triethyl 2-fluoro-2-phosphonoacetate was prepared in one step from dibromofluoromethyl phosphonate and ethyl chloroformate.

Triethyl 2-fluoro-2-phosphonoacetate synthesis method

The invention discloses a triethyl 2-fluoro-2-phosphonoacetate synthesis method. According to the present invention, ethyl bromofluoroacetate and triethyl phosphite are used as starting raw materials,and are subjected to a Michaelis-Arbuzov reaction to synthesize triethyl 2-fluoro-2-phosphonoacetate, wherein the steps are less, such that the obtained by-products are few, and the yield is increased.

INHIBITORS OF BRUTON'S TYROSINE KINASE AND METHODS OF THEIR USE

Compounds of formula (I') and methods of their use and preparation, as well as compositions comprising compounds of formula (I').

INHIBITORS OF BRUTON'S TYROSINE KINASE AND METHODS OF THEIR USE

The present disclosure is directed to compounds of formula I and methods of their use and preparation, as well as compositions comprising compounds of formula I.

HETEROARYL SUBSTITUTED AMINOPYRIDINE COMPOUNDS

Disclosed are compounds of Formula (I) Formula(I) or salts thereof, wherein HET is a heteroaryl selected from oxazolyl, pyrazolyl, imidazo[l,2-b]pyridazin-3-yl, and pyrazolo[l,5-a]pyrimidin-3-yl, wherein said heteroaryl is attached to the pyridinyl group in the compound of Formula (I) by a carbon ring atom in the heteroaryl and wherein said heteroaryl is substituted with zero to 2 Rb; and R1, R3, and Rb are define herein. Also disclosed are methods of using such compounds as modulators of IRAK4, and pharmaceutical compositions comprising such compounds. These compounds are useful in treating, preventing, or slowing inflammatory and autoimmune diseases, or in the treatment of cancer.

INHIBITORS OF BRUTON'S TYROSINE KINASE

Disclosed herein are compounds that inhibit Bruton's tyrosine kinase (Btk). Also described are irreversible inhibitors of Btk. In addition, reversible inhibitors of Btk are also described. Also disclosed are pharmaceutical compositions that include the compounds. Methods of using the Btk inhibitors are disclosed, alone or in combination with other therapeutic agents, for the treatment of autoimmune diseases or conditions, heteroimmune diseases or conditions, cancer, including lymphoma, and inflammatory diseases or conditions.