Sodium Sulfate → HCID 86621692, compound

HRID 2408442Notes

Reaction equation

HRID 2408442 reaction equation
[C:1]([O:5][C:6](=[O:34])[NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[NH:14][C:15](=[O:33])/[CH:16]=[CH:17]/[C:18]1[CH:22]=[CH:21][N:20]([S:23]([C:26]2[CH:31]=[CH:30][C:29](I)=[CH:28][CH:27]=2)(=[O:25])=[O:24])[CH:19]=1)([CH3:4])([CH3:3])[CH3:2].[CH3:35][O:36][C:37]1[CH:42]=[CH:41][C:40](B(O)O)=[CH:39][N:38]=1.S([O-])([O-])(=O)=O.[Na+].[Na+]>C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl.C(COC)OC>[C:1]([O:5][C:6](=[O:34])[NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[NH:14][C:15](=[O:33])/[CH:16]=[CH:17]/[C:18]1[CH:22]=[CH:21][N:20]([S:23]([C:26]2[CH:31]=[CH:30][C:29]([C:40]3[CH:39]=[N:38][C:37]([O:36][CH3:35])=[CH:42][CH:41]=3)=[CH:28][CH:27]=2)(=[O:25])=[O:24])[CH:19]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 24436Sodium SulfateHCID 2734368(6-Methoxypyridin-3-yl)boronic acidHCID 86621693HCID 86621693, compound

Product 1

HCID 86621692HCID 86621692, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

To mixture of 0.3 g (2-{(E)-3-[1-(4-Iodo-benzenesulfonyl)-1H-pyrrol-3-yl]-allanoylamino}-phenyl)-carbamic acid tert-butyl ester, 0.116 g 2-methoxy-5-pyridineboronic acid and 11 ml dimethoxyethane are added under an inert gas atmosphere 0.9 ml of an aqueous solution of 2N sodium sulfate and 70 mg of bis-(triphenylphosphine)palladium-(II)chlorid. The mixture is refluxed for 24 h and after filtration and evaporation the residue is extracted between ethyl acetate and a 5% aqueous solution of sodium bicarbonate. The organic phase is dried and evaporated and the crude product is purified by silica gel flash chromatography. 87% of a colorless solid are obtained.

Workup

  1. temperatureThe mixture is refluxed for 24 h
  2. filtrationafter filtration and evaporation the residue
  3. extractionis extracted between ethyl acetate
  4. customThe organic phase is dried
  5. customevaporated
  6. customthe crude product is purified by silica gel flash chromatography

Sources & evidence

ORD record
ord-43e29782bc454bea8539081949114577
Source dataset
uspto-grants-2014_08
Patent number
US08815855B2

Reaction notes

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