N,N'-Dimethylethylenediamine → 1-[3-Bromo-5-(pyridine-3-carbonyl)-phenyl]-pyrrolidin-2-one

HRID 1784862Notes

Reaction equation

HRID 1784862 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:9]([C:11]2[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=2)=[O:10])[CH:5]=[C:6]([Br:8])[CH:7]=1.C(=O)([O-])[O-].[Cs+].[Cs+].CNCCNC.[NH:29]1[CH2:33][CH2:32][CH2:31][C:30]1=[O:34]>[Cu]I.O1CCOCC1>[Br:8][C:6]1[CH:7]=[C:2]([N:29]2[CH2:33][CH2:32][CH2:31][C:30]2=[O:34])[CH:3]=[C:4]([C:9]([C:11]2[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=2)=[O:10])[CH:5]=1

Participants

7

Reactant 4

HCID 8070N,N'-DimethylethylenediamineHCID 10796Cesium carbonateHCID 120252-PyrrolidoneHCID 106649193-(3,5-Dibromobenzoyl)pyridine

Product 1

HCID 574709891-[3-Bromo-5-(pyridine-3-carbonyl)-phenyl]-pyrrolidin-2-oneYield 7.2%

Reagents, catalysts & solvents 2

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

Conditions

Temperature
80 °C

Procedure

To a nitrogen-flushed tube were added 0.20 grams (0.72 mmol) (3,5-dibromo-phenyl)-pyridin-3-yl-methanone, 0.137 g (0.72 mmol) copper (I) iodide, 0.235 (0.72 mmol) cesium carbonate, 0.063 g (0.72 mmol) N,N′-dimethyl-ethane-1,2-diamine, 0.061 g (0.72 mmol) pyrrolidin-2-one and 5 mL dioxane. The tube was sealed and heated at 80° C. overnight. The reaction mixture was allowed to cool, and was filtered. The volatiles were removed under reduced pressure and the resulting material was chromatographed on silica gel with 2% methanol/chloroform to give 0.018 g of 1-[3-bromo-5-(pyridine-3-carbonyl)-phenyl]-pyrrolidin-2-one. This material was converted to 1-[3-(1H-indol-4-yl)-5-(pyridine-3-carbonyl)-phenyl]-pyrrolidin-2-one as described in Example 75. 1H NMR (400 MHz, CD3OD): δ 9.01 (s, 1H), 8.79 (s, 1H), 8.26-8.31 (m, 2H), 8.06 (s, 1H), 7.86 (s, 1H), 7.62 (s, 1H), 7.42 (d, J=8.0 Hz, 1H), 7.30 (d, J=3.1 Hz, 1H), 7.19 (t, J=7.5 Hz, 1H), 7.14 (d, J=7.2 Hz, 1H), 6.67 (d, J=3.1 Hz, 1H), 4.03 (t, J=7.0 Hz, 2H), 2.63 (t, J=8.1 Hz, 2H), 2.16-2.26 (m, 2H).

Workup

  1. customTo a nitrogen-flushed tube
  2. customThe tube was sealed
  3. temperatureto cool
  4. filtrationwas filtered
  5. customThe volatiles were removed under reduced pressure
  6. customthe resulting material was chromatographed on silica gel with 2% methanol/chloroform

Sources & evidence

ORD record
ord-c4902999dbd14def8e1e030623f1b029
Source dataset
uspto-grants-2009_03
Patent number
US07504401B2

Reaction notes

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