6-Bromoindole → Benzyl 3-(1-(6-bromo-1H-indol-3-yl)-2-nitroethyl)-2-methylphenylcarbamate
Reaction equation
[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[CH:7][NH:8]2)=[CH:4][CH:3]=1.[CH3:11][C:12]1[C:17](/[CH:18]=[CH:19]/[N+:20]([O-:22])=[O:21])=[CH:16][CH:15]=[CH:14][C:13]=1[NH:23][C:24](=[O:33])[O:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.C(OCC)(=O)C.CCCCCC>C1COCC1.CN1C(=O)CCC1>[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH:18]([C:17]3[C:12]([CH3:11])=[C:13]([NH:23][C:24](=[O:33])[O:25][CH2:26][C:27]4[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=4)[CH:14]=[CH:15][CH:16]=3)[CH2:19][N+:20]([O-:22])=[O:21])=[CH:7][NH:8]2)=[CH:4][CH:3]=1Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 120 °C
Procedure
A mixture of 6-bromo-1H-indole (2.82 g, 14.41 mmol) and (E)-benzyl 2-methyl-3-(2-nitrovinyl)phenylcarbamate (3.0 g, 9.61 mmol) was dissolved in THF (50 mL) and NMP (0.5 mL). The THF was removed under vacuum, and the residue was heated at 120° C. for 16 hr and then at 125° C. for 6 hr. Upon cooling to room temperature, the mixture was dissolved in THF (50 mL). The resulting solution was diluted with ethyl acetate (250 mL), washed with water (3×80 mL) and brine (60 mL), and dried over anhydrous MgSO4. The desired product (3.00 g, 5.90 mmol, 61.4% yield) was isolated as a beige solid by ISCO (300 g silica gel, 25-60 ethyl acetate/hexane).
Workup
- customThe THF was removed under vacuum
- temperatureUpon cooling to room temperature
- dissolutionthe mixture was dissolved in THF (50 mL)
- additionThe resulting solution was diluted with ethyl acetate (250 mL)
- washwashed with water (3×80 mL) and brine (60 mL)
- dry with materialdried over anhydrous MgSO4
Sources & evidence
- ORD record
- ord-db4c5c9ed2604de7a4172fbe64095eb5
- Source dataset
- uspto-grants-2014_04
- Patent number
- US08685969B2
Reaction notes
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