Ammonium Chloride → Benzyl 3-(2-amino-1-(6-bromo-1H-indol-3-yl)ethyl)-2-methylphenylcarbamate
Reaction equation
[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH:11]([C:16]3[C:17]([CH3:33])=[C:18]([NH:22][C:23](=[O:32])[O:24][CH2:25][C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)[CH:19]=[CH:20][CH:21]=3)[CH2:12][N+:13]([O-])=O)=[CH:7][NH:8]2)=[CH:4][CH:3]=1.[Cl-].[NH4+]>CO.O1CCCC1.C(OCC)(=O)C.[Zn]>[NH2:13][CH2:12][CH:11]([C:16]1[C:17]([CH3:33])=[C:18]([NH:22][C:23](=[O:32])[O:24][CH2:25][C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH:19]=[CH:20][CH:21]=1)[C:6]1[C:5]2[C:9](=[CH:10][C:2]([Br:1])=[CH:3][CH:4]=2)[NH:8][CH:7]=1Participants
7
Reactant 2
Product 1
Reagents, catalysts & solvents 4
Procedure
To a mixture of benzyl 3-(1-(6-bromo-1H-indol-3-yl)-2-nitroethyl)-2-methylphenylcarbamate (3.00 g, 5.90 mmol) and ammonium chloride (4.42 g, 83 mmol) in methanol (100 mL) and tetrahydrofuran (100 mL) at 0° C. was added zinc dust (5.40 g, 83 mmol) in one portion. The mixture was stirred at room temperature for 7 hr, then diluted with ethyl acetate (100 mL) and filtered through CELITE®. The filtrate was concentrated under vacuum. To the residue was added water (60 mL), and the mixture was extracted with ethyl acetate (4×80 mL). The combined extract was washed with brine (60 mL) and dried over anhydrous MgSO4. Removal of solvent under vacuum provided the desired product (2.82 g, 5.89 mmol, 100% yield) as a beige solid.
Workup
- filtrationfiltered through CELITE®
- concentrationThe filtrate was concentrated under vacuum
- additionTo the residue was added water (60 mL)
- extractionthe mixture was extracted with ethyl acetate (4×80 mL)
- extractionThe combined extract
- washwas washed with brine (60 mL)
- dry with materialdried over anhydrous MgSO4
- customRemoval of solvent under vacuum
Sources & evidence
- ORD record
- ord-aa6bbcaf81304e459a1623123cc0292d
- Source dataset
- uspto-grants-2014_04
- Patent number
- US08685969B2
Reaction notes
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