Cesium carbonate → HCID 62480333, compound

HRID 1038046Notes

Reaction equation

HRID 1038046 reaction equation
[CH3:1][C@@H:2]1[CH2:7][NH:6][CH2:5][CH2:4][NH:3]1.Br[C:9]1[S:10][CH:11]=[CH:12][N:13]=1.C1(C2C=CC=CC=2)C=CC=CC=1P(C(C)(C)C)C(C)(C)C.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:1][CH:2]1[NH:3][CH2:4][CH2:5][N:6]([C:9]2[S:10][CH:11]=[CH:12][N:13]=2)[CH2:7]1

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 764302-BromothiazoleHCID 27342152-(Di-tert-butylphosphino)biphenylHCID 73304342-Methylpiperazine, (R)-

Product 1

HCID 62480333HCID 62480333, compoundYield 26.4%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 312751,4-DioxaneSolvent

Procedure

A mixture of 2(R)-methyl piperazine (300 mg, 3 mmol), 2-bromo thiazole (0.27 ml, 3 mmol), (2-biphenylyldi-tert-butylphosphine (134 mg, 0.449 mmol), palladium acetate (101 mg, 0.45 mmol), and cesium carbonate (1.46 g, 4.49 mmol) in dioxane 25 ml (v/v 5/1) was kept at reflux temperature for 2 hours, then cooled to room temperature, then filtered through celite, then concentrated and then purified by chromatography eluting with 12% MeOH/MeCl2/NH4OH to yield the product as a white solid (145 mg, 26%).

Workup

  1. temperatureat reflux temperature for 2 hours
  2. filtrationfiltered through celite
  3. concentrationconcentrated
  4. custompurified by chromatography
  5. washeluting with 12% MeOH/MeCl2/NH4OH

Sources & evidence

ORD record
ord-f3d040932ea447408f4da463d3654b27
Source dataset
uspto-grants-2013_10
Patent number
US08546404B2

Reaction notes

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