Bromomethylcyclopropane → 5-Bromo-1-(cyclopropylmethyl)-1,2-dihydropyridin-2-one

HRID 1626928Notes

Reaction equation

HRID 1626928 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([OH:8])=[N:6][CH:7]=1.[CH3:9][C:10]([CH3:13])([O-])[CH3:11].[K+].BrCC1CC1>CN(C=O)C.CCOC(C)=O>[Br:1][C:2]1[CH:3]=[CH:4][C:5](=[O:8])[N:6]([CH2:9][CH:10]2[CH2:13][CH2:11]2)[CH:7]=1

Participants

6

Reactant 3

HCID 81503BromomethylcyclopropaneHCID 23665647Potassium tert-butoxideHCID 178515818HCID 178515818, compound

Product 1

HCID 596357015-Bromo-1-(cyclopropylmethyl)-1,2-dihydropyridin-2-one

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 5-bromopyridin-2-ol (1.0 g, 5.75 mmol) in DMF (10 mL) at RT, potassium tert-butoxide (0.68 g, 6.07 mmol) was added and the mixture was stirred for 30 min. To this mixture, (bromomethyl)cyclopropane (1.03 g, 8.62 mmol) was added, and the resulting mixture was stirred at 70° C. for 2 h. The mixture was allowed to cool to RT, diluted with EtOAc (50 mL) and quenched with water (20 mL). The organic layer was washed with water (2×20 mL) and brine (20 mL), dried over anhydrous MgSO4 and filtered. The filtrate was concentrated in vacuo to afford 5-bromo-1-(cyclopropylmethyl)pyridin-2(1H)-one.

Workup

  1. stirringthe resulting mixture was stirred at 70° C. for 2 h
  2. customquenched with water (20 mL)
  3. washThe organic layer was washed with water (2×20 mL) and brine (20 mL)
  4. dry with materialdried over anhydrous MgSO4
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-49cd24bfa3e24a0db496b2a74d60aa83
Source dataset
uspto-grants-2014_07
Patent number
US08785470B2

Reaction notes

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