N,N'-Dimethylethylenediamine → HCID 86679116, compound

HRID 2277648Notes

Reaction equation

HRID 2277648 reaction equation
Br[C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Br:8])[CH:7]=1.[OH:9][CH2:10][C@H:11]1[NH:15][C:14](=[O:16])[CH2:13][CH2:12]1.C(=O)([O-])[O-].[K+].[K+].CNCCNC>O1CCOCC1.[Cu]I>[Br:8][C:6]1[CH:7]=[C:2]([N:15]2[C@H:11]([CH2:10][OH:9])[CH2:12][CH2:13][C:14]2=[O:16])[CH:3]=[N:4][CH:5]=1

Participants

7

Reactant 4

HCID 8070N,N'-DimethylethylenediamineHCID 11430Potassium CarbonateHCID 693693,5-DibromopyridineHCID 643511(S)-5-(Hydroxymethyl)-2-pyrrolidinone

Product 1

HCID 86679116HCID 86679116, compoundYield 25%

Reagents, catalysts & solvents 2

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

Conditions

Temperature
110 °C

Procedure

In a sealed tube, 3,5-dibromopyridine (0.5 g, 2.11 mmol) was combined with (S)-5-(hydroxymethyl)pyrrolidin-2-one (0.243 g, 2.11 mmol), copper (I) iodide (0.040 g, 0.021 mmol), potassium carbonate (0.583 g, 4.22 mmol) and N,N′-dimethylethylenediamine (0.037 g, 0.042 mmol) in 1,4-dioxane (20 mL). The reaction mixture was heated at 110° C. overnight. The mixture was cooled to room temperature, filtered through dicalite and washed with DCM. The residue was purified by silica gel flash chromatography eluting with a 0 to 10% MeOH-DCM gradient to give the title compound (0.140 g, 25%) as a light yellow oil. MS: 271.1, 273.1 (M+H+).

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. filtrationfiltered through dicalite
  3. washwashed with DCM
  4. customThe residue was purified by silica gel flash chromatography
  5. washeluting with a 0 to 10% MeOH-DCM gradient

Sources & evidence

ORD record
ord-8cbd8f372654489b9596591d0476de8f
Source dataset
uspto-grants-2015_09
Patent number
US09133158B2

Reaction notes

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