Hydrochloric Acid → 1-(2-Bromopyridin-4-yl)-3-phenylpropan-1-one
Reaction equation
[C:1]1([CH2:7][CH2:8][Mg]Cl)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:11][C:12]1[CH:13]=[C:14]([CH:21]=[CH:22][N:23]=1)[C:15](N(OC)C)=[O:16].C1([Mg]Cl)C=CC=CC=1.Cl.[OH-].[Na+]>C1COCC1>[Br:11][C:12]1[CH:13]=[C:14]([C:15](=[O:16])[CH2:8][CH2:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH:21]=[CH:22][N:23]=1Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 25 °C
Procedure
1.0 mL of 1.0 N phenyethylmagnesium chloride in THF was added dropwise to a −78° C. solution of 200 mg of 2-bromo-N-methoxy-N-methylisonicotinamide in 6 mL of THF. The solution was allowed to warm to 25° C. After 10 minutes the solution was cooled back to −78° C. and an additional 1.0 mL of 1.0 N phenylmagnesium chloride in THF was added. The mixture was warmed to 25° C. and after 10 minutes 10 mL of 1.0 N hydrochloric acid was added. The solution was then made basic with excess aqueous sodium hydroxide solution and the mixture was partitioned between ethyl acetate and water. The aqueous phase was washed with ethyl acetate and the combined organic extracts were dried over sodium sulfate. The solvent was evaporated and the residue was chromatographed on silica gel to give 168 mg of product.
Workup
- temperatureAfter 10 minutes the solution was cooled back to −78° C.
- additionwas added
- customthe mixture was partitioned between ethyl acetate and water
- washThe aqueous phase was washed with ethyl acetate
- dry with materialthe combined organic extracts were dried over sodium sulfate
- customThe solvent was evaporated
- customthe residue was chromatographed on silica gel
Sources & evidence
- ORD record
- ord-5d39cc02e1f44cfc86015decefc9bf49
- Source dataset
- uspto-grants-2014_12
- Patent number
- US08916569B2
Reaction notes
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