Ammonium Chloride → 5-Fluoro-7-[(methylsulfanyl)methyl]-1H-indole
Reaction equation
[CH:1]([Mg]Br)=[CH2:2].[F:5][C:6]1[CH:11]=[CH:10][C:9]([N+:12]([O-])=O)=[C:8]([CH2:15][S:16][CH3:17])[CH:7]=1.[Cl-].[NH4+]>O1CCCC1>[F:5][C:6]1[CH:11]=[C:10]2[C:9](=[C:8]([CH2:15][S:16][CH3:17])[CH:7]=1)[NH:12][CH:2]=[CH:1]2Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -40 °C
Procedure
180 ml (180 mmol) of a 1N solution of vinylmagnesium bromide in tetrahydrofuran were added dropwise to a solution of 9.00 g (44.7 mmol) of the compound from Example 4A in 100 ml of tetrahydrofuran under argon at −40° C., and the mixture was stirred at −40° C. for 3 h. The reaction mixture was then added to saturated aqueous ammonium chloride solution and extracted with tert-butyl methyl ether. The combined organic phases were washed with saturated aqueous sodium chloride solution, dried over sodium sulfate, filtered and concentrated. The residue was purified by flash chromatography (mobile phase: petroleum ether/ethyl acetate 9/1) to result in 5.00 g (57% of theory) of the title compound.
Workup
- extractionextracted with tert-butyl methyl ether
- washThe combined organic phases were washed with saturated aqueous sodium chloride solution
- dry with materialdried over sodium sulfate
- filtrationfiltered
- concentrationconcentrated
- customThe residue was purified by flash chromatography (mobile phase: petroleum ether/ethyl acetate 9/1)
Sources & evidence
- ORD record
- ord-998a515ac89f477188dc28ef2be113f0
- Source dataset
- uspto-grants-2011_11
- Patent number
- US08063234B2
Reaction notes
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