Hydrochloric Acid → 5-fluoro-3-methyl-2,3-dihydro-1H-indole
Reaction equation
B.[F:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=O)[CH:6]2[CH3:13].CO.Cl>C1COCC1>[F:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH2:7][CH:6]2[CH3:13]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 70 °C
Procedure
Under an argon atmosphere 18 mL (18 mmol) of a 1M borane in THF solution was added dropwise to 1.5 g (9.1 mmol) 5-fluoro-3-methyl-1,3-dihydro-indol-2-one in 50 mL THF. The reaction mixture was stirred for 2 h at 70° C., cooled to 0° C. and combined with 10 mL methanol and then with 30 mL semi-concentrated hydrochloric acid solution. The reaction mixture was refluxed for 1 h with stirring, cooled and the organic phase was eliminated using the rotary evaporator. The aqueous phase was extracted with ethyl acetate. The aqueous phase was made alkaline with an aqueous 4M sodium hydroxide solution and extracted with dichloromethane. The organic phase was dried on sodium sulphate, filtered off and evaporated down.
Workup
- temperaturecooled to 0° C.
- temperatureThe reaction mixture was refluxed for 1 h
- stirringwith stirring
- temperaturecooled
- customthe rotary evaporator
- extractionThe aqueous phase was extracted with ethyl acetate
- extractionextracted with dichloromethane
- customThe organic phase was dried on sodium sulphate
- filtrationfiltered off
- customevaporated down
Sources & evidence
- ORD record
- ord-075c97acf3964a028a8b4ae314e4ad98
- Source dataset
- uspto-grants-2014_09
- Patent number
- US08829006B2
Reaction notes
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