2,6-Lutidine → HCID 86720756, compound
Reaction equation
[CH3:1][C:2]1[C:3]([C:9](=[O:11])[CH3:10])=[N:4][CH:5]=[C:6]([CH3:8])[N:7]=1.N1C(C)=CC=CC=1C.FC(F)(F)S(O[Si](C)(C)C)(=O)=O.[Br:32]N1C(=O)CCC1=O>O.C(Cl)(Cl)Cl>[Br:32][CH2:10][C:9]([C:3]1[C:2]([CH3:1])=[N:7][C:6]([CH3:8])=[CH:5][N:4]=1)=[O:11]Participants
Procedure
To a chloroform (2.0 mL) solution of 1-(3,5-dimethylpyrazin-2-yl)ethanone (41 mg), under ice cooling in a nitrogen atmosphere, 2,6-lutidine (54 μL) and trimethylsilyl trifluoromethanesulfonate (59 μL) were added, and the resultant was stirred for 1 hour. Then, N-bromosuccinimide (53 mg) was added thereto, and the resultant was stirred at room temperature for 30 minutes. Water was added to the reaction solution, and the resultant was stirred for 10 minutes, followed by extraction with chloroform. An organic layer was separated using a phase separator, and the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography (OH-type silica gel; hexane/ethyl acetate-gradient elution=95/5→67/33) to obtain the title compound (35 mg) as a crude product.
Workup
- stirringthe resultant was stirred at room temperature for 30 minutes
- stirringthe resultant was stirred for 10 minutes
- extractionfollowed by extraction with chloroform
- customAn organic layer was separated
- distillationthe solvent was distilled off under reduced pressure
- customThe obtained residue was purified by silica gel column chromatography (OH-type silica gel; hexane/ethyl acetate-gradient elution=95/5→67/33)
Sources & evidence
- ORD record
- ord-1f15b60d629f45c194c10d70ea4e7344
- Source dataset
- uspto-grants-2015_06
- Patent number
- US09045466B2
Reaction notes
Loading…