Cesium carbonate → HCID 68854348, compound

HRID 1500265Notes

Reaction equation

HRID 1500265 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N+:8]([O-:10])=[O:9].C([O-])([O-])=O.[Cs+].[Cs+].[C:17]([O:21][C:22]([N:24]1[CH2:29][CH2:28][NH:27][CH:26]([CH3:30])[CH2:25]1)=[O:23])([CH3:20])([CH3:19])[CH3:18]>CC([O-])=O.CC([O-])=O.[Pd+2].C1(C)C=CC=CC=1>[C:17]([O:21][C:22]([N:24]1[CH2:29][CH2:28][N:27]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=2[N+:8]([O-:10])=[O:9])[CH:26]([CH3:30])[CH2:25]1)=[O:23])([CH3:20])([CH3:18])[CH3:19]

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 113411-Bromo-2-nitrobenzeneHCID 2756810tert-Butyl 3-methylpiperazine-1-carboxylate

Product 1

HCID 68854348HCID 68854348, compound

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolvent

Procedure

1-Bromo-2-nitrobenzene (2.00 mmol, 404 mg), Pd(OAc)2 (0.100 mmol, 22.5 mg), Palucki-Phos (0.120 mmol, 45.8 mg) and Cs2CO3 (3 mmol, 1 g) were loaded into a Schlenk tube containing a stir bar. The tube was capped with a rubber septum, evacuated and refilled with nitrogen. 3-Methyl-piperazine-1-carboxylic acid tert-butyl ester (0.48 mL, 2.5 mmol) and toluene (3 mL) were added to the reaction through the septum via syringe and the tube was sealed with a Teflon screw cap under a flow of nitrogen, and put into an oil bath at 100° C. The reaction was allowed to stir at this temperature for about 15 hours and was then was cooled to room temperature and filtered through celite. The filtrate was concentrated in vacuo and the resulting residue was purified using flash column chromatography on silica gel (eluent: Hexane/EtOAc (5:1) to provide 3-methyl-4-(2-nitro-phenyl)-piperazine-carboxylic acid tert-butyl ester.

Workup

  1. additioncontaining a stir bar
  2. customThe tube was capped with a rubber septum
  3. customevacuated
  4. additionrefilled with nitrogen
  5. customscrew cap under a flow of nitrogen
  6. customput into an oil bath at 100° C
  7. filtrationfiltered through celite
  8. concentrationThe filtrate was concentrated in vacuo
  9. customthe resulting residue was purified

Sources & evidence

ORD record
ord-233a33308f614c5cb30194cae4b11462
Source dataset
uspto-grants-2015_12
Patent number
US09206142B2

Reaction notes

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