Sodium Carbonate → HCID 22636224, compound

HRID 2415894Notes

Reaction equation

HRID 2415894 reaction equation
[F:1][C:2]([F:42])([F:41])[CH2:3][NH:4][C:5]([C:7]1([CH2:20][CH2:21][CH2:22][CH2:23][N:24]2[CH2:29][CH2:28][N:27]([C:30]3[CH:39]=[CH:38][C:37]4[C:32](=[C:33](Br)[CH:34]=[CH:35][CH:36]=4)[N:31]=3)[CH2:26][CH2:25]2)[C:19]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[C:13]2[C:8]1=[CH:9][CH:10]=[CH:11][CH:12]=2)=[O:6].[C:43]1(OB(O)O)[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1>[F:1][C:2]([F:42])([F:41])[CH2:3][NH:4][C:5]([C:7]1([CH2:20][CH2:21][CH2:22][CH2:23][N:24]2[CH2:29][CH2:28][N:27]([C:30]3[CH:39]=[CH:38][C:37]4[C:32](=[C:33]([C:43]5[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=5)[CH:34]=[CH:35][CH:36]=4)[N:31]=3)[CH2:26][CH2:25]2)[C:19]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[C:13]2[C:8]1=[CH:9][CH:10]=[CH:11][CH:12]=2)=[O:6]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 78412Phenyl dihydrogen orthoborateHCID 22636332HCID 22636332, compound

Product 1

HCID 22636224HCID 22636224, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A reaction mixture of 0.2 g (0.314 mmol) of 9-{4-[4-(8-bromo-quinolin-2-yl)-piperazin-1-yl]-butyl}-9H-fluorene-9-carboxylic acid-(2,2,2-trifluoro-ethyl)-amide, 0.033 g (0.267 mmol) of phenylboric acid, 0.018 g (0.016 mmol) of tetrakis triphenyl palladium and 0.2 ml of a 2 M sodium carbonate solution in 3 ml of toluene is refluxed for 20 hours under nitrogen. The solvent is distilled off. The residue is purified by column chromatography on silica gel (eluant: cyclohexane/ethyl acetate=3:2).

Workup

  1. temperatureis refluxed for 20 hours under nitrogen
  2. distillationThe solvent is distilled off
  3. customThe residue is purified by column chromatography on silica gel (eluant: cyclohexane/ethyl acetate=3:2)

Sources & evidence

ORD record
ord-8d2569df2aaa452a8a421890c3c76139
Source dataset
uspto-grants-2004_11
Patent number
US06821967B2

Reaction notes

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