t-Butyl bromide → 3-(tert-Butyl)-6-nitro-1h-indole
Reaction equation
[N+:1]([C:4]1[CH:12]=[C:11]2[C:7]([CH:8]=[CH:9][NH:10]2)=[CH:6][CH:5]=1)([O-:3])=[O:2].CCN(C(C)C)C(C)C.[C:22](Br)([CH3:25])([CH3:24])[CH3:23]>CCCC[N+](CCCC)(CCCC)CCCC.[I-].C1(C)C=CC=CC=1.[O-]S(C(F)(F)F)(=O)=O.[Zn+2].[O-]S(C(F)(F)F)(=O)=O>[C:22]([C:8]1[C:7]2[C:11](=[CH:12][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=2)[NH:10][CH:9]=1)([CH3:25])([CH3:24])[CH3:23]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 120 °C
Procedure
To a mixture of 6-nitroindole (1.0 g, 6.2 mmol), zinc triflate (2.1 g, 5.7 mmol), and TBAI (1.7 g, 5.2 mmol) in anhydrous toluene (11 mL) was added DIEA (1.5 g, 11 mmol) at room temperature under nitrogen. The reaction mixture was stirred for 10 min at 120° C., followed by the addition of t-butyl bromide (0.71 g, 5.2 mmol). The resulting mixture was stirred for 45 min at 120° C. The solid was filtered off and the filtrate was concentrated to dryness. The residue was purified by column chromatography on silica gel (petroleum ether/ethyl acetate=20:1) to give 3-tert-butyl-6-nitro-1H-indole (0.25 g, 19%) as a yellow solid. 1H-NMR (CDCl3) δ 8.32 (d, J=2.1 Hz, 1H), 8.00 (dd, J=2.1, 14.4 Hz, 1H), 7.85 (d, J=8.7 Hz, 1H), 7.25 (s, 1H), 1.46 (s, 9H).
Workup
- stirringThe resulting mixture was stirred for 45 min at 120° C
- filtrationThe solid was filtered off
- concentrationthe filtrate was concentrated to dryness
- customThe residue was purified by column chromatography on silica gel (petroleum ether/ethyl acetate=20:1)
Sources & evidence
- ORD record
- ord-0560ba8f86c14ac3a112798d1a4ff18b
- Source dataset
- uspto-grants-2013_12
- Patent number
- US08598181B2
Reaction notes
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