Hydrochloric Acid → (2E)-3-[2-Bromo-4-(trifluoromethyl)phenyl]-N-indol-5-ylprop-2-enamide
Reaction equation
[Br:1][C:2]1[CH:10]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:8]=[CH:7][C:3]=1[C:4](O)=O.Br[C:16]1[CH:21]=[C:20]([C:22](F)(F)F)[CH:19]=[CH:18][C:17]=1C.[Mn]([O-])(=O)(=O)=O.[CH2:32]([N+:34](CC)(CC)CC)[CH3:33].Cl.[OH:42]S([O-])=O.[Na+].[N:47]1[CH:52]=CC=CC=1>>[Br:1][C:2]1[CH:10]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:8]=[CH:7][C:3]=1/[CH:4]=[CH:33]/[C:32]([NH:34][C:16]1[CH:21]=[C:20]2[C:19](=[CH:18][CH:17]=1)[NH:47][CH:52]=[CH:22]2)=[O:42]Participants
Reactant 6
Product 1
Conditions
- Temperature
- 70 °C
Procedure
2-Bromo-4-(trifluoromethyl)benzoic acid. To a solution of 2-bromo-1-methyl-4-trifluoromethylbenzene (7.6 g, 32 mmol, ABCR) in pyridine (75 mL) was added tetraethylammonium permanganate (24 g, 96 mmol, prepared according to the procedure of Sala, et al. J. Chem. Soc., Chem. Comm. 1978, 253). The reaction mixture was warmed to 70° C. and stirred at that temperature for 30 h. The reaction mixture was allowed to cool to 25° C. and poured into an ice bath containing cond HCl (150 mL) and NaHSO3 (150 g). The mixture turned to a clear aqueous solution and was extracted with EtOAc (4×200 mL). The combined extracts were washed with satd NaCl (200 mL), dried over Na2SO4, filtered and concentrated in vacuo to provide the title product as a white solid. MS (ESI, neg. ion) m/z: 267 (M−1).
Workup
- customprepared
- temperatureto cool to 25° C.
- additionpoured into an ice bath
- extractionwas extracted with EtOAc (4×200 mL)
- washThe combined extracts were washed with satd NaCl (200 mL)
- dry with materialdried over Na2SO4
- filtrationfiltered
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-8ead1b3012a44d2ab1273c223c778832
- Source dataset
- uspto-grants-2009_09
- Patent number
- US07582657B2
Reaction notes
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