Potassium Carbonate → (3-Acetyl-5-trifluoromethoxy-indol-1-yl)-acetic acid tert-butyl ester
Reaction equation
[F:1][C:2]([F:17])([F:16])[O:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][CH:8]=[C:7]2[C:13](=[O:15])[CH3:14].C([O-])([O-])=O.[K+].[K+].Br[CH2:25][C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27]>CC#N>[C:29]([O:28][C:26](=[O:27])[CH2:25][N:9]1[C:10]2[C:6](=[CH:5][C:4]([O:3][C:2]([F:1])([F:16])[F:17])=[CH:12][CH:11]=2)[C:7]([C:13](=[O:15])[CH3:14])=[CH:8]1)([CH3:32])([CH3:31])[CH3:30]Participants
5
Conditions
- Temperature
- 90 °C
Procedure
To a solution of 1-(5-trifluoromethoxy-1H-indol-3-yl)-ethanone (0.50 g, 2.06 mmol) in CH3CN (10 mL) was added K2CO3 (0.313 g, 2.26 mmol) and tert-butyl 2-bromoacetate (0.334 mL, 2.26 mmol). The reaction mixture was stirred at 90° C. overnight. The reaction mixture was filtered, and the filtrate was diluted with CH2Cl2. The organics were washed with 1M aqueous HCl solution (5 mL) and saturated aqueous NaHCO3 solution (5 mL). The organic layer was dried (phase separator) and evaporated in vacuo to afford the title compound as a yellowish oil: MS: 358.0 [M+H]+; tR (HPLC conditions c): 5.66 min. The material thus obtained was used directly in the next step without further purification.
Workup
- filtrationThe reaction mixture was filtered
- additionthe filtrate was diluted with CH2Cl2
- washThe organics were washed with 1M aqueous HCl solution (5 mL) and saturated aqueous NaHCO3 solution (5 mL)
- customThe organic layer was dried (phase separator)
- customevaporated in vacuo
Sources & evidence
- ORD record
- ord-a92e47bc456043d59fbcd88e88346fb5
- Source dataset
- uspto-grants-2015_07
- Patent number
- US09085555B2
Reaction notes
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