Cesium carbonate → HCID 58902457, compound

HRID 1640162Notes

Reaction equation

HRID 1640162 reaction equation
Br[C:2]1[CH:3]=[C:4]([N:12]2[C:16]([CH3:17])=[CH:15][CH:14]=[C:13]2[CH3:18])[CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1.[CH3:19][N:20]1[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]1.C(=O)([O-])[O-].[Cs+].[Cs+]>C1(C)C=CC=CC=1.C(Cl)Cl.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH3:18][C:13]1[N:12]([C:4]2[CH:3]=[C:2]([N:23]3[CH2:24][CH2:25][N:20]([CH3:19])[CH2:21][CH2:22]3)[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=2)[C:16]([CH3:17])=[CH:15][CH:14]=1

Participants

7

Reactant 3

HCID 10796Cesium carbonateHCID 531671-MethylpiperazineHCID 589023221-[3-bromo-5-(trifluoromethyl)phenyl]-2,5-dimethyl-1H-pyrrole

Product 1

HCID 58902457HCID 58902457, compoundYield 32%

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 1-[3-bromo-5-(trifluoromethyl)phenyl]-2,5-dimethyl-1H-pyrrole (510 mg, 1.6 mmol), 1-methylpiperazine (210 μL, 1.9 mmol), Pd2(dba)3 (70 mg, 0.08 mmol), 2′-BINAP (100 mg, 0.2 mmol) and cesium carbonate (730 mg, 2.2 mmol) in toluene (5.1 mL) was subjected to MWI at 150° C. for 10 min. The reaction mixture was diluted with DCM and washed with brine. The residue was purified by column chromatography to give 1-[3-(2,5-dimethyl-1H-pyrrol-1-yl)-5-(trifluoromethyl)phenyl]-4methylpiperazine (172 mg, 32%) as a yellow solid. LCMS: (FA) ES+ 338.3.

Workup

  1. washwashed with brine
  2. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-e9111529a17f400385b92350f6d14f12
Source dataset
uspto-grants-2012_02
Patent number
US08110687B2

Reaction notes

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