4,4-Dimethylpiperidin-2-one → 1-(5-Bromo-pyrazin-2-yl)-4,4-dimethyl-pyrrolidin-2-one

HRID 629250Notes

Reaction equation

HRID 629250 reaction equation
[Br:1][C:2]1[CH:7]=[N:6][C:5](I)=[CH:4][N:3]=1.C[C:10]1([CH3:17])[CH2:15][CH2:14][NH:13][C:12](=[O:16])[CH2:11]1>C1(C)C=CC=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.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1(P(C2C=CC=CC=2)C2C3OC4C(=CC=CC=4P(C4C=CC=CC=4)C4C=CC=CC=4)C(C)(C)C=3C=CC=2)C=CC=CC=1>[Br:1][C:2]1[N:3]=[CH:4][C:5]([N:13]2[CH2:14][C:10]([CH3:15])([CH3:17])[CH2:11][C:12]2=[O:16])=[N:6][CH:7]=1

Participants

6

Reactant 2

HCID 122020974,4-Dimethylpiperidin-2-oneHCID 219312002-Bromo-5-iodopyrazine

Product 1

HCID 575167811-(5-Bromo-pyrazin-2-yl)-4,4-dimethyl-pyrrolidin-2-oneYield 53.2%

Reagents, catalysts & solvents 3

HCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)CatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolvent

Procedure

To a well stirred suspension of 2-bromo-5-iodopyrazine (300 mg, 1.05 mmol), 4,4-dimethylpiperidin-2-one (155 mg, 1.37 mmol, 1.3 equiv.) and 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (xantphos) (24.4 mg, 0.042 mmol, 0.04 equiv.) in 4 ml of toluene were added under argon atmosphere tris(dibenzylideneacetone)dipalladium(0) (Pd2(dba)3), (19.3 mg, 0.021 mmol, 0.02 equiv.) and the mixture was stirred for 5 hours at 100° C. The crude mixture was adsorbed on silicagel and purified by flash chromatography over a 20 g silicagel column using a 2:1 heptane/ethyl acetate mixture as eluant. The title compound (151 mg, 53% yield) was obtained as a white solid, MS: m/e=270.1, 272.1 (M+H+).

Workup

  1. stirringthe mixture was stirred for 5 hours at 100° C
  2. custompurified by flash chromatography over a 20 g silicagel column

Sources & evidence

ORD record
ord-90d8c3cdd8c34458bef0553588793808
Source dataset
uspto-grants-2016_04
Patent number
US09315498B2

Reaction notes

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