Ammonium Acetate → 1-[1-(3-Fluorophenyl)-3-methyl-1H-indol-2-yl]ethanamine
Reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10]([CH3:17])=[C:9]2[C:18](=O)[CH3:19])[CH:5]=[CH:6][CH:7]=1.C([O-])(=O)C.[NH4+].C([BH3-])#[N:27].[Na+]>CO.C(#N)C>[F:1][C:2]1[CH:3]=[C:4]([N:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10]([CH3:17])=[C:9]2[CH:18]([NH2:27])[CH3:19])[CH:5]=[CH:6][CH:7]=1Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 65 °C
Procedure
A mixture of 1-[1-(3-fluorophenyl)-3-methyl-1H-indol-2-yl]ethanone (0.165 g, 0.617 mmol) and ammonium acetate (0.476 g, 6.17 mmol) in methanol (2.0 mL) and acetonitrile (2.0 mL) was heated at 65° C. in a sealed tube for 1 hour. After cooling to room temperature, sodium cyanoborohydride (0.12 g, 1.9 mmol) was added to the resultant mixture. The reaction was heated at 65° C. over the weekend. The reaction was cooled to room temperature and quenched with saturated NaHCO3 solution and then extracted with dichloromethane, dried over MgSO4 and concentrated to give the crude amine (0.16 g), which was used directly in next step. LCMS calculated for C17H18FN2(M+H)+: m/z=269.1. Found: 252.1.
Workup
- temperatureAfter cooling to room temperature
- temperatureThe reaction was heated at 65° C. over the weekend
- temperatureThe reaction was cooled to room temperature
- customquenched with saturated NaHCO3 solution
- extractionextracted with dichloromethane
- dry with materialdried over MgSO4
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-d0f917a4a43740829fa8f313a35afcb8
- Source dataset
- uspto-grants-2015_06
- Patent number
- US09062055B2
Reaction notes
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