N,N'-Dimethylethylenediamine → HCID 71547397, compound

HRID 868809Notes

Reaction equation

HRID 868809 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([C:8]#[C:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[N:6][CH:7]=1.[CH3:16][C:17]1([CH3:23])[CH2:21][NH:20][C:19](=[O:22])[CH2:18]1.C(=O)([O-])[O-].[K+].[K+].CNCCNC>O1CCOCC1.[Cu]I>[CH3:16][C:17]1([CH3:23])[CH2:21][N:20]([C:2]2[CH:7]=[N:6][C:5]([C:8]#[C:9][C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)=[CH:4][CH:3]=2)[C:19](=[O:22])[CH2:18]1

Participants

7

Reactant 4

HCID 8070N,N'-DimethylethylenediamineHCID 11430Potassium CarbonateHCID 6375934,4-Dimethyl-2-pyrrolidinoneHCID 16067786HCID 16067786, compound

Product 1

HCID 71547397HCID 71547397, compoundYield 67%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

To a suspension of 5-bromo-2-phenylethynyl-pyridine (Example 1, step 1) (40 mg, 0.155 mmol), 4,4-dimethylpyrrolidine-2-one (21 mg, 0.186 mmol, 1.2 equiv.), potassium carbonate (64 mg, 0.465 mmol, 3 equiv.) and N,N′-dimethylethylenediamine (1.4 mg, 0.015 mmol, 0.1 equiv.) in 1 ml of dioxane was added under argon atmosphere copper(I)iodide (3 mg, 0.015 mmol, 0.1 equiv.). The mixture was stirred overnight at 100° C. The reaction mixture was cooled and extracted with saturated NaHCO3 solution and two times with ethyl acetate. The organic layers were extracted with brine, combined, dried over sodium sulfate and evaporated to dryness. The crude product was purified by flash chromatography on a silica gel column eluting with a heptane:ethyl acetate gradient 100:0 to 30:70. The desired 4,4-dimethyl-1-(6-phenylethynyl-pyridin-3-yl)-pyrrolidin-2-one (30 mg, 67% yield) was obtained as a white solid, MS: m/e=291.1 (M+H30).

Workup

  1. temperatureThe reaction mixture was cooled
  2. extractionextracted with saturated NaHCO3 solution and two times with ethyl acetate
  3. extractionThe organic layers were extracted with brine
  4. dry with materialdried over sodium sulfate
  5. customevaporated to dryness
  6. customThe crude product was purified by flash chromatography on a silica gel column
  7. washeluting with a heptane

Sources & evidence

ORD record
ord-dfb9b859b1374c16ac44a8c74871df42
Source dataset
uspto-grants-2015_03
Patent number
US08969338B2

Reaction notes

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