N,N'-Dimethylethylenediamine → HCID 86720659, compound

HRID 2201864Notes

Reaction equation

HRID 2201864 reaction equation
Br[C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([C:9]([N:11]2[C:19]3[CH:18]=[CH:17][N:16]=[CH:15][C:14]=3[CH:13]=[CH:12]2)=[O:10])=[C:4]([Cl:20])[CH:3]=1.[N-:21]=[N+]=[N-].[Na+].CNCCNC>C(O)C.O.[Cu](I)I>[NH2:21][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([C:9]([N:11]2[C:19]3[CH:18]=[CH:17][N:16]=[CH:15][C:14]=3[CH:13]=[CH:12]2)=[O:10])=[C:4]([Cl:20])[CH:3]=1

Participants

7

Reactant 3

HCID 8070N,N'-DimethylethylenediamineHCID 33557Sodium AzideHCID 71061918HCID 71061918, compound

Product 1

HCID 86720659HCID 86720659, compoundYield 45.4%

Reagents, catalysts & solvents 3

HCID 83717Copper iodideCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of (4-bromo-2,6-dichlorophenyl)(1H-pyrrolo[3,2-c]pyridin-1-yl)methanone (200 mg, 0.54 mmol), sodium azide (105 mg, 1.62 mmol), copper (II) iodide (30 mg, 0.16) and N,N′-dimethylethane-1,2-diamine (26 mg, 0.32 moles) in ethanol (2 mL) and water (0.5 mL) was heated in a sealed vial at 90° C. for 16 hours. The reaction mixture was concentrated to remove ethanol and the residue was diluted with water (50 mL) and extracted with ethyl acetate (2×50 mL). The combined organic portion was dried over anhydrous sodium sulphate and concentrated under vacuum to give the crude product which was purified by silica gel column chromatography using ethyl acetate and hexane as eluent to yield (4-amino-2,6-dichlorophenyl)(1H-pyrrolo[3,2-c]pyridin-1-yl)methanone (75 mg, 45%).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customto remove ethanol
  3. additionthe residue was diluted with water (50 mL)
  4. extractionextracted with ethyl acetate (2×50 mL)
  5. dry with materialThe combined organic portion was dried over anhydrous sodium sulphate
  6. concentrationconcentrated under vacuum
  7. customto give the crude product which
  8. customwas purified by silica gel column chromatography

Sources & evidence

ORD record
ord-d55d2895faf24f5e8263ed9b1f74f55d
Source dataset
uspto-grants-2016_06
Patent number
US09364466B2

Reaction notes

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