Potassium Carbonate → HCID 67362972, compound

HRID 245770Notes

Reaction equation

Cl[C:2]1[C:3]([CH2:8][NH:9][C:10]([CH:12]2[CH2:16][C:15](=[O:17])[N:14]([CH3:18])[CH2:13]2)=[O:11])=[N:4][CH:5]=[CH:6][N:7]=1.[C:19](=O)([O-])[O-].[K+].[K+].CB1OB(C)OB(C)O1>O1CCOCC1.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2].[Pd](Cl)Cl>[CH3:18][N:14]1[C:15](=[O:17])[CH2:16][CH:12]([C:10]([NH:9][CH2:8][C:3]2[C:2]([CH3:19])=[N:7][CH:6]=[CH:5][N:4]=2)=[O:11])[CH2:13]1

Participants

Conditions

Temperature: 100 °C

Procedure

To a stirred suspension of N-((3-chloropyrazin-2-yl)methyl)-1-methyl-5-oxopyrrolidine-3-carboxamide (700 mg, 2.61 mmol) and potassium carbonate (540 mg, 3.91 mmol) in 1,4-dioxan (10 ml) under a nitrogen atmosphere was added trimethylboroxine (981 mg, 7.82 mmol) and 1,1′-bis-(diphenylphosphino)-ferrocene) palladium dichloride (214 mg, 0.261 mmol). The reaction was heated at 100° C. for one hour. Then the reaction mixture was filtered over celite and the celite was rinsed three times with ethyl acetate. Subsequently, the combined filtrates were concentrated in vacuo and the crude product was purified by column chromatography (silica gel; dichloromethane/methanol 96/5) to give 1-methyl-N-((3-methylpyrazin-2-yl)methyl)-5-oxopyrrolidine-3-carboxamide (440 mg).

Workup

filtrationThen the reaction mixture was filtered over celite
washthe celite was rinsed three times with ethyl acetate
concentrationSubsequently, the combined filtrates were concentrated in vacuo
customthe crude product was purified by column chromatography (silica gel; dichloromethane/methanol 96/5)

Sources & evidence

ORD record: ord-9cb0bfef34ad451bb31147656c839058
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08658794B2

Reaction notes

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