Ethanol → 1-amino-8-fluoro-5H-pyrido[4,3-b]indole-4-carboxamide
Reaction equation
Cl[C:2]1[C:14]2[C:13]3[CH:12]=[C:11]([F:15])[CH:10]=[CH:9][C:8]=3[NH:7][C:6]=2[C:5]([C:16]#[N:17])=[CH:4][N:3]=1.CCO.[NH4+:21].[OH-:22]>O>[NH2:21][C:2]1[C:14]2[C:13]3[CH:12]=[C:11]([F:15])[CH:10]=[CH:9][C:8]=3[NH:7][C:6]=2[C:5]([C:16]([NH2:17])=[O:22])=[CH:4][N:3]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 150 °C
Procedure
A mixture of 1-chloro-8-fluoro-5H-pyrido[4,3-b]indole-4-carbonitrile in a 1:1 (v/v) mixture of EtOH and conc. NH4OH (0.13 M) was heated in a microwave reactor at 150° C. for 1 h in a sealed tube. After cooling to room temperature, the suspension was diluted with H2O and filtered. The crude material was placed in a flask cooled to 0° C. before conc. H2SO4 (excess) was added dropwise under vigorous stirring. The final mixture was warmed to room temperature and, after 4 h, poured carefully into a diluted aqueous solution of NH4OH cooled to 0° C. The precipitate was collected by filtration and was purified by flash chromatography (20-50% ethanol in CH2Cl2) to provide the title compound as an off-white solid.
Workup
- temperatureAfter cooling to room temperature
- filtrationfiltered
- customThe crude material was placed in a flask
- temperaturecooled to 0° C. before conc. H2SO4 (excess)
- additionwas added dropwise under vigorous stirring
- temperatureThe final mixture was warmed to room temperature and, after 4 h
- additionpoured carefully into a diluted aqueous solution of NH4OH
- temperaturecooled to 0° C
- filtrationThe precipitate was collected by filtration
- customwas purified by flash chromatography (20-50% ethanol in CH2Cl2)
Sources & evidence
- ORD record
- ord-8dc3e159e9de47cca79425bd2d34e4e6
- Source dataset
- uspto-grants-2013_08
- Patent number
- US08518964B2
Reaction notes
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