Dimethylformamide → 3-Methyl-5-trifluoromethyl-indol-1-ylamine
Reaktionsgleichung
[H-].[Na+].[CH3:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([C:13]([F:16])([F:15])[F:14])[CH:11]=2)[NH:6][CH:5]=1.C[N:18](C=O)C>>[CH3:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([C:13]([F:16])([F:14])[F:15])[CH:11]=2)[N:6]([NH2:18])[CH:5]=1Komponenten
Reaktionsbedingungen
- Temperatur
- 0 °C
Versuchsvorschrift
60% NaH (1.21 g, 30.2 mmol) is added to a stirred solution of 3-methyl-5-trifluoromethyl-1H-indole (400 mg, 2.01 mmol) in DMF (6 mL) at 0° C. in portions. The mixture is stirred at 0° C. for 1 h. HOSA (1.14 g, 10.0 mmol) is added in portions at 0° C. and the mixture is allowed to warm to rt over 2 h. The reaction is quenched with aqueous saturated ammonium chloride, extracted with extracted three times with DCM. The combined organic layer is dried (Na2SO4), filtered and concentrated. The residue is chromatographed through silica gel eluting with 0-40% EtOAc in heptane to afford 3-methyl-5-trifluoromethyl-indol-1-ylamine (223 mg, 52%). MS: 215 (M+H); 1H NMR (300 MHz, CDCl3): δ=7.84 (s, 1H), 7.48 (s, 2H), 7.04 (s, 1H), 4.77 (s, 2H), 2.34 (s, 3H).
Aufarbeitung
- additionHOSA (1.14 g, 10.0 mmol) is added in portions at 0° C.
- temperatureto warm to rt over 2 h
- customThe reaction is quenched with aqueous saturated ammonium chloride
- extractionextracted
- extractionwith extracted three times with DCM
- dry with materialThe combined organic layer is dried (Na2SO4)
- filtrationfiltered
- concentrationconcentrated
- customThe residue is chromatographed through silica gel eluting with 0-40% EtOAc in heptane
Quellen und Nachweise
- ORD-Eintrag
- ord-8298464c34864bee9fb8c42bad62ee8f
- Quelldatensatz
- uspto-grants-2012_09
- Patentnummer
- US08258130B2
Notizen zur Reaktion
Wird geladen…