Sodium hydride → HCID 59301375, compound

HRID 2236199Notes

Reaction equation

HRID 2236199 reaction equation
[OH:1][CH2:2][CH2:3][N:4]([CH3:14])[C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][N:6]=1.[H-].[Na+].Br[CH2:18][CH:19]1[CH2:21][CH2:20]1>C1COCC1.CN(C=O)C.CCOC(C)=O>[CH:19]1([CH2:18][O:1][CH2:2][CH2:3][N:4]([CH3:14])[C:5]2[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][N:6]=2)[CH2:21][CH2:20]1

Participants

7

Reactant 3

HCID 24758Sodium hydrideHCID 81503BromomethylcyclopropaneHCID 1176762-(N-Methyl-N-(5-nitro-2-pyridyl)amino)ethanol

Product 1

HCID 59301375HCID 59301375, compound

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

(2-Hydroxy-ethyl)-methyl-(5-nitro-pyridin-2-yl)-amine (98.5 mg, 0.5 mmol) in THF (10 mL) and DMF (2 mL) was stirred with 60% NaH in oil (32 mg, 0.8 mmol) for 1 hr. The mixture was cooled and to this was added bromomethylcyclopropane (0.685 mg, 5 mmol). The reaction mixture was allowed to stir overnight. The mixture was diluted with EtOAc, extracted with H2O and dried over MgSO4. The EtOAc was filtered, evaporated to dryness and used without further purification. Yield: 82 mg. ES-MS calcd for C12H17N3O3 (m/e) 251.29, obsd 252.1 (M+H).

Workup

  1. temperatureThe mixture was cooled
  2. extractionextracted with H2O
  3. dry with materialdried over MgSO4
  4. filtrationThe EtOAc was filtered
  5. customevaporated to dryness
  6. customused without further purification

Sources & evidence

ORD record
ord-da047221b483406c81a2254cb9f5b122
Source dataset
uspto-grants-2010_05
Patent number
US07714126B2

Reaction notes

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