Potassium Carbonate → HCID 43078820, compound

HRID 2236197Notes

Reaction equation

HRID 2236197 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=1.[C@@H:11]([NH2:15])([CH2:13][CH3:14])[CH3:12].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.CCOC(C)=O>[CH:11]([NH:15][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=1)([CH2:13][CH3:14])[CH3:12]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 782402-Bromo-5-nitropyridineHCID 67137532-Butanamine, (S)-

Product 1

HCID 43078820HCID 43078820, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

2-Bromo-5-nitropyridine (341 mg, 1.68 mmol), (S)-(+)-sec butylamine (123 mg, 1.68 mmol), and finely ground potassium carbonate (707 mg, 5.1 mmol) were heated to 80° C. in 15 mL anhydrous DMF for 3.5 hrs. The mixture was diluted with EtOAc, extracted with H2O and dried over MgSO4. The EtOAc layer was filtered, evaporated to dryness and purified by flash chromatography to yield 233 mg. ES-MS calcd for C9H13N3O2 (m/e) 195.22, obsd 196.1 (M+H).

Workup

  1. extractionextracted with H2O
  2. dry with materialdried over MgSO4
  3. filtrationThe EtOAc layer was filtered
  4. customevaporated to dryness
  5. custompurified by flash chromatography
  6. customto yield 233 mg

Sources & evidence

ORD record
ord-733aa99ff1bb439b8a81ed3f77728a58
Source dataset
uspto-grants-2010_05
Patent number
US07714126B2

Reaction notes

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