187523-35-9

Usage

Uses

Neuroprotectant (opener of large conductance, calcium-activated (maxi-K) K+channels.

InChI:InChI=1/C16H10ClF4NO2/c1-24-13-5-3-9(17)7-11(13)15(18)10-4-2-8(16(19,20)21)6-12(10)22-14(15)23/h2-7H,1H3,(H,22,23)/t15-/m1/s1

Upstream product

• 635305-45-2 2-(5-chloro-2-(methoxy)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 183720-28-7 3-(5-Chloro-2-methoxyphenyl)-3-fluoro-1,3-dihydro-6-(trifluoromethyl)-2H-indol-2-one 
• 89694-48-4 5-chloro-2-methoxyphenyl boronic acid 
• 206194-02-7 (S)-(-)-5-Chloro-2-methoxy-α-fluoro-α-[2-nitro-4-(trifluoromethyl)phenyl]benzeneacetic acid 
• 206194-00-5 5-chloro-α-fluoro-2-methoxy-α-[2-nitro-4-(trifluoromethyl)-phenyl]benzeneacetic acid,methyl ester 
• 26939-01-5 5-chloro-2-methoxyphenylacetic acid,methyl ester 
• 367-86-2 1-fluoro-2-nitro-4-trifluoromethyl-benzene 
• 183720-15-2 3-(5-Chloro-2-methoxyphenyl)-1,3-dihydro-3-hydroxy-6-(trifluoromethyl)-2H-indol-2-one 
• 159684-36-3 (2-tert-Butoxycarbonylamino-4-trifluoromethyl-phenyl)-oxo-acetic acid ethyl ester 
• 109134-07-8 t-butyl<3-(trifluoromethyl)phenyl>-carbamate 
• 98-16-8 3-trifluoromethylaniline 
• 343-69-1 6-(Trifluoromethyl)-1H-indol-2,3-dione 
• 862907-03-7 tert-butyl 3-(5-chloro-2-methoxyphenyl)-6-(trifluoromethyl)-2-oxoindoline-1-carboxylate 
• 862907-04-8 tert-butyl (+)-3-(5-chloro-2-methoxyphenyl)-3-fluoro-6-(trifluoromethyl)-2-oxoindoline-1-carboxylate 

Downstream Products

• 607740-49-8 (S)-3-(5-Chloro-2-methoxy-phenyl)-3-fluoro-1-hydroxymethyl-6-trifluoromethyl-1,3-dihydro-indol-2-one 
• 607740-52-3 (S)-3-(5-chloro-2-methoxyphenyl)-3-fluoro-2-oxo-6-(trifluoromethyl)-indoline 1-carbonyl chloride 
• 864775-17-7 (S)-(4-(benzyloxy)-4-oxobutanoyloxy)methyl 3-(5-chloro-2-methoxyphenyl)-3-fluoro-2-oxo-6-(trifluoromethyl)indoline-1-carboxylate 
• 864775-44-0 (S)-tert-butyl 2-((S)-3-(5-chloro-2-methoxyphenyl)-3-fluoro-2-oxo-6-(trifluoromethyl)indoline-1-carboxamido)propanoate 
• 728024-04-2 1-(4-(R),5-(R)-bis-benzyloxy-6-(R)-benzyloxymethyl-3-(R)-hydroxy-tetrahydro-pyran-2-(R)-yl)-3-(S)-(5-chloro-2-methoxy-phenyl)-3-fluoro-6-trifluoromethyl-1,3-dihydro-indol-2-one 
• 864775-40-6 (S)-(3-(5-chloro-2-methoxyphenyl)-3-fluoro-2-oxo-6-(trifluoromethyl)indolin-1-yl)methyl 4-(chloromethyl)benzoate 
• 864775-42-8 (S)-(3-(5-chloro-2-methoxyphenyl)-3-fluoro-2-oxo-6-(trifluoromethyl)indolin-1-yl)methyl 3-(chloromethyl)benzoate 
• 864774-72-1 C₃₀H₂₇ClF₄N₂O₆ 

Relevant academic research and scientific papers

Enantioselective fluorination mediated by N-fluoroammonium salts of cinchona alkaloids: First enantioselective synthesis of BMS-204352 (maxipost)

We have employed a cinchona alkaloid/Select-fluor-mediated enantioselective fluorination of the oxindole 2 to achieve the first enantioslective synthesis of BMS-204352 (MaxiPost, S-1), an effective opener of maxi-K channels. Fluorination occurred to produce S-1 with 84% ee using the bis-cinchona alkaloid (DHQ)2AQN. Recrystallization produced enantiomerically pure (>99% ee) product. Quinidine-mediated fluorination of 2 gave the (R)-antipode of 1 with 68% ee.

Novel synthesis method for Flindokalner raceme

The invention discloses a novel synthesis method for a Flindokalner raceme. The method comprises the steps: subjecting 3-fluoro-3-(2,2,2-trifluoro-1,1-dihydroxyethyl)-6(trifluoromethyl)2H-indol-2-one, which serves as a raw material, to a bromation reactio

Highly enantioselective fluorination of unprotected 3-substituted oxindoles: One-step synthesis of BMS 204352 (MaxiPost)

The catalytic enantioselective fluorination of N-H-free 3-substituted oxindoles was accomplished by a Sc(III)/N,N′-dioxide complex. Under mild reaction conditions, a series of 3-aryl- and 3-alkyl-3-fluoro-2-oxindoles were obtained in excellent yields (up to 98%) and enantioselectivities (up to 99% ee) by using N-fluorobisbenzenesulfonimide (NFSI) as the fluorination agent. MaxiPost was synthesized efficiently in 81% yield with 96% ee.

Highly enantioselective fluorination of unprotected 3-substituted oxindoles: One-step synthesis of BMS 204352 (MaxiPost)

The catalytic enantioselective fluorination of N-H-free 3-substituted oxindoles was accomplished by a Sc(III)/N,N′-dioxide complex. Under mild reaction conditions, a series of 3-aryl- and 3-alkyl-3-fluoro-2-oxindoles were obtained in excellent yields (up to 98%) and enantioselectivities (up to 99% ee) by using N-fluorobisbenzenesulfonimide (NFSI) as the fluorination agent. MaxiPost was synthesized efficiently in 81% yield with 96% ee.

PREPARATION OF 3-FLUORO OXINDOLE DERIVATIVES

The present invention relates to novel itermediates of formula (1) wherein the wavy bond ( SIMILAR SIMILAR ) represents the racemate, the (R)-enantiomer or the (S)-enantiomer; and R is hydrogen, a carboxyl-protecting group or a cation of an addition salt;

Catalytic enantioselective fluorination of oxindoles

We have developed a highly efficient catalytic enantioselective fluorination of oxindole derivatives. In the presence of a catalytic amount of chiral Pd complex 2 (2.5 mol %), various substrates, including aryl- and alkyl-substituted oxindoles, were fluor

Carbohydrate prodrugs of fluorooxindoles

The present invention provides novel prodrug derivatives of fluorooxindoles having the general Formula I wherein the wavy bond () represents the racemate, the (R)-enantiomer or the (S)-enantiomer, and R1, R2, R3, R4

Enantioselective synthesis of BMS-204352 (MaxiPost) using N-fluoroammonium salts of cinchona alkaloids (F-CA-BF4).

The enantioselective synthesis of a potent Maxi-K potassium channel opener (BMS-204352) mediated by N-fluoroammonium salts of cinchona alkaloids is described. Two synthetic pathways were evaluated. An ee as high as 88% was achieved (>99% after a single re

The synthesis and characterization of BMS-204352 (MaxiPost) and related 3-fluorooxindoles as openers of maxi-K potassium channels

3-Aryl-3-fluorooxindoles can be efficiently synthesized in two steps by the addition of an aryl Grignard to an isatin, followed by treatment with DAST. Oxindole 1 (BMS-204352; MaxiPost) can be isolated using chiral HPLC or prepared by employing chiral res