Flindokalner

Base Information

• Chemical Name: Flindokalner
• CAS No.: 187523-35-9
• Molecular Formula: C16H10 Cl F4 N O2
• Molecular Weight: 359.708
• UNII: J57O328W4W
• DSSTox Substance ID: DTXSID70870176
• Nikkaji Number: J1.532.916E
• Wikidata: Q27077683
• NCI Thesaurus Code: C76778
• Pharos Ligand ID: JWT88K5Y6DCR
• ChEMBL ID: CHEMBL266510
• Mol file: 187523-35-9.mol

Synonyms:(5-chloro-2-methoxyphenyl)-1,3-dihydro-3-fluoro-6-(trifluoromethyl)-2H-indol-2-one;BMS 204352;BMS-204352;BMS204352;MaxiPost

Chemical Property of Flindokalner

Chemical Property:

• Vapor Pressure: 7.82E-08mmHg at 25°C
• Boiling Point: 436.9°Cat760mmHg
• PKA: 10.43±0.40(Predicted)
• Flash Point: 218°C
• PSA: 38.33000
• Density: 1.5g/cm³
• LogP: 4.67060
• XLogP3: 4.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 2
• Exact Mass: 359.0336189
• Heavy Atom Count: 24
• Complexity: 503

Purity/Quality:

>98% ^*data from raw suppliers

MaxiPost ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=C(C=C(C=C1)Cl)C2(C3=C(C=C(C=C3)C(F)(F)F)NC2=O)F
• Isomeric SMILES: COC1=C(C=C(C=C1)Cl)[C@]2(C3=C(C=C(C=C3)C(F)(F)F)NC2=O)F
• Recent ClinicalTrials: Hypersensitivity to Opening of BKCa Channels in Post-Traumatic Headache
• Uses: Neuroprotectant (opener of large conductance, calcium-activated (maxi-K) K+channels.

Technology Process of Flindokalner

There total 23 articles about Flindokalner which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 83.0%

(S)-(-)-5-Chloro-2-methoxy-α-fluoro-α-[2-nitro-4-(trifluoromethyl)phenyl]benzeneacetic acid (206194-02-7) → (S)-(+)-3-(5-chloro-2-methoxyphenyl)-3-fluoro-1,3-dihydro-6-(trifluoromethyl)-2H-indol-2-one (187523-35-9,187523-36-0)

Guidance literature:

(S)-(-)-5-Chloro-2-methoxy-α-fluoro-α-[2-nitro-4-(trifluoromethyl)phenyl]benzeneacetic acid; With sodium dithionite; sodium hydrogencarbonate; In tetrahydrofuran; water; for 1.25h;

With hydrogenchloride; In methanol; ethyl acetate; at 20 - 60 ℃; for 0.0833333h;

Reference yield: 81.0%

(+)-3-(5-chloro-2-methoxyphenyl)-1,3-dihydro-6-(trifluoromethyl)-2H-indol-2-one (385764-29-4,385764-30-7,183720-16-3) → (S)-(+)-3-(5-chloro-2-methoxyphenyl)-3-fluoro-1,3-dihydro-6-(trifluoromethyl)-2H-indol-2-one (187523-35-9,187523-36-0)

Guidance literature:

(+)-3-(5-chloro-2-methoxyphenyl)-1,3-dihydro-6-(trifluoromethyl)-2H-indol-2-one; With C₃₉H₆₀N₄O₄; scandium tris(trifluoromethanesulfonate); In chloroform; at 35 ℃; for 0.5h; Inert atmosphere;

With sodium carbonate; N-fluorobis(benzenesulfon)imide; In chloroform; at 0 ℃; for 72h; enantioselective reaction; Inert atmosphere;

DOI:10.1021/jo301705t DOI:10.1021/jo301705t

Reference yield:

6-(Trifluoromethyl)-1H-indol-2,3-dione (343-69-1) → (S)-(+)-3-(5-chloro-2-methoxyphenyl)-3-fluoro-1,3-dihydro-6-(trifluoromethyl)-2H-indol-2-one (187523-35-9,187523-36-0)

Guidance literature:

Multi-step reaction with 5 steps

1.1: NaH / tetrahydrofuran / 1 h / 0 °C

1.2: 81 percent / tetrahydrofuran / 4 h / -20 - 20 °C

2.1: 76 percent / Et₃SiH; TFA / 48 h / 110 - 120 °C

3.1: 80 percent / EtMgBr / tetrahydrofuran / 3 h / 20 °C

4.1: N-fluorobenzenesulfonimide; [Pd2((S)-DM-BINAP)2(μ-OH)2](2+)*2TfO(1-) / acetone / 18 h / 0 °C

5.1: TFA / CH₂Cl₂ / 8 h / 20 °C

With triethylsilane; [Pd2((S)-DM-BINAP)2(μ-OH)2](2+)*2TfO(1-); ethylmagnesium bromide; sodium hydride; N-fluorobis(benzenesulfon)imide; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; acetone;

DOI:10.1021/ja0513077

upstream raw materials:

3-(5-Chloro-2-methoxyphenyl)-1,3-dihydro-3-hydroxy-6-(trifluoromethyl)-2H-indol-2-one

(+)-3-(5-chloro-2-methoxyphenyl)-1,3-dihydro-6-(trifluoromethyl)-2H-indol-2-one

tert-butyl (+)-3-(5-chloro-2-methoxyphenyl)-3-fluoro-6-(trifluoromethyl)-2-oxoindoline-1-carboxylate

tert-butyl 3-(5-chloro-2-methoxyphenyl)-6-(trifluoromethyl)-2-oxoindoline-1-carboxylate

Downstream raw materials:

(S)-3-(5-Chloro-2-methoxy-phenyl)-3-fluoro-1-hydroxymethyl-6-trifluoromethyl-1,3-dihydro-indol-2-one

(S)-3-(5-chloro-2-methoxyphenyl)-3-fluoro-2-oxo-6-(trifluoromethyl)-indoline 1-carbonyl chloride

(S)-(3-(5-chloro-2-methoxyphenyl)-3-fluoro-2-oxo-6-(trifluoromethyl)indolin-1-yl)methyl 3-(chloromethyl)benzoate

(S)-(3-(5-chloro-2-methoxyphenyl)-3-fluoro-2-oxo-6-(trifluoromethyl)indolin-1-yl)methyl 4-(chloromethyl)benzoate

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