Ethanol → HCID 67261454, compound
Reaction equation
[C:1]([C:5]1[C:13]2[C:8](=[CH:9][C:10]([N+:18]([O-])=O)=[C:11]([C:14]([F:17])([F:16])[F:15])[CH:12]=2)[NH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].O.O.Cl[Sn]Cl.C(O)C>CCOC(C)=O>[C:1]([C:5]1[C:13]2[C:8](=[CH:9][C:10]([NH2:18])=[C:11]([C:14]([F:15])([F:16])[F:17])[CH:12]=2)[NH:7][CH:6]=1)([CH3:4])([CH3:2])[CH3:3]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 62 °C
Procedure
A microwave vial charged with 3-tert-butyl-6-nitro-5-(trifluoromethyl)-1H-indole (95 mg, 0.3319 mmol), SnCl2.2H2O (375 mg, 1.66 mmol) and ethanol (1 mL), was sealed and heated at 62° C. for 3 h. The reaction was cooled to room temperature, diluted with EtOAc and quenched with saturated NaHCO3 solution until the pH was 7. The reaction mixture was then filtered through a plug of celite. The layers were separated and the organic layer was dried over Na2SO4, filtered and concentrated. The residue was purified via silica gel column chromatography using 0 to 40% EtOAc in hexanes to obtain 3-tert-butyl-5-(trifluoromethyl)-1H-indol-6-amine. LC/MS: m/z 257.3 (M+H)+ at 1.54 min (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)).
Workup
- customwas sealed
- temperatureThe reaction was cooled to room temperature
- customquenched with saturated NaHCO3 solution until the pH was 7
- filtrationThe reaction mixture was then filtered through a plug of celite
- customThe layers were separated
- dry with materialthe organic layer was dried over Na2SO4
- filtrationfiltered
- concentrationconcentrated
- customThe residue was purified via silica gel column chromatography
Sources & evidence
- ORD record
- ord-c3c7fc0f502a467b88e4ca335c306738
- Source dataset
- uspto-grants-2014_08
- Patent number
- US08802700B2
Reaction notes
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