Potassium Carbonate → HCID 70652019, compound
Reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][NH:5][C:4](=[O:8])[CH:3]=1.I[CH:10]1[CH2:13][O:12][CH2:11]1.C([O-])([O-])=O.[K+].[K+]>CN(C)C=O>[Br:1][C:2]1[CH:7]=[CH:6][N:5]([CH:10]2[CH2:13][O:12][CH2:11]2)[C:4](=[O:8])[CH:3]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 100 °C
Procedure
A mixture of 4-bromopyridin-2(1H)-one (173 mg), 3-iodooxetane (184 mg), and K2CO3 (414 mg) in N,N-dimethylformamide (15 mL) was stirred at 100° C. for 2 h. The reaction mixture was stirred at room temperature for one more hour and then quenched with H2O (30 mL). The resulting mixture was extracted with ethyl acetate (3×20 mL) and the combined organic phase was dried (Na2SO4) and concentrated to give the crude product, which was purified by preparative TLC to give the title compound. Yield: 68 mg (30% of theory).
Workup
- stirringThe reaction mixture was stirred at room temperature for one more hour
- customquenched with H2O (30 mL)
- extractionThe resulting mixture was extracted with ethyl acetate (3×20 mL)
- dry with materialthe combined organic phase was dried (Na2SO4)
- concentrationconcentrated
- customto give the crude product, which
- customwas purified by preparative TLC
Sources & evidence
- ORD record
- ord-518daf41e8b24effaaf73567a268755d
- Source dataset
- uspto-grants-2015_01
- Patent number
- US08933072B2
Reaction notes
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