Ammonium Chloride → 7-Chloro-2,3-dimethyl-1H-pyrrolo[2,3-c]pyridine
Reaction equation
[Cl:1][C:2]1[C:7]([N+:8]([O-])=O)=[CH:6][CH:5]=[CH:4][N:3]=1.[CH3:11][C:12]([Mg]Br)=[CH:13][CH3:14].[Cl-].[NH4+]>O1CCCC1>[Cl:1][C:2]1[N:3]=[CH:4][CH:5]=[C:6]2[C:13]([CH3:14])=[C:12]([CH3:11])[NH:8][C:7]=12Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -20 °C
Procedure
2-Chloro-3-nitropyridine (8 g, 50.46 mmol) was dissolved in anhydrous tetrahydrofuran (200 ml) at nitrogen atmosphere. 1-Methyl-1-propenyl magnesium bromide (0.5M in tetrahydrofuran solution, 252 ml, 126.15 mmol) was slowly added at −78° C. to the solution. The reaction mixture was stirred for 2 hours at −20° C. and 20% ammonium chloride solution was added thereto. The reaction mixture was extracted with ethyl acetate and then concentrated under reduced pressure. The resulting residue was purified with silica gel column chromatography (ethyl acetate/n-hexane=1/3, v/v) to give 2.73 g of the titled compound as a pale yellow solid. (Yield: 30%)
Workup
- extractionThe reaction mixture was extracted with ethyl acetate
- concentrationconcentrated under reduced pressure
- customThe resulting residue was purified with silica gel column chromatography (ethyl acetate/n-hexane=1/3
Sources & evidence
- ORD record
- ord-6907ebe3232e4e1b93b716d9c602bd04
- Source dataset
- uspto-grants-2012_05
- Patent number
- US08188114B2
Reaction notes
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