Water → 1-Cyanomethyl-5-trifluoromethoxy-1H-indole-2-carboxylic acid ethyl ester
Reaction equation
[H-].[Na+].[CH2:3]([O:5][C:6]([C:8]1[NH:9][C:10]2[C:15]([CH:16]=1)=[CH:14][C:13]([O:17][C:18]([F:21])([F:20])[F:19])=[CH:12][CH:11]=2)=[O:7])[CH3:4].Cl[CH2:23][C:24]#[N:25].O>CN(C=O)C>[CH2:3]([O:5][C:6]([C:8]1[N:9]([CH2:23][C:24]#[N:25])[C:10]2[C:15]([CH:16]=1)=[CH:14][C:13]([O:17][C:18]([F:21])([F:19])[F:20])=[CH:12][CH:11]=2)=[O:7])[CH3:4]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 75 °C
Procedure
To a solution of sodium hydride (0.58 g in DMF (12 mL) at 0° C. was slowly added a solution of 5-trifluoromethoxy-1H-indole-2-carboxylic acid ethyl ester (2.64 g) in DMF (12 mL) keeping the temperature below 7.5° C. After gas evolution ceased, chloroacetonitrile was added, and the reaction mixture was stirred for 2 hours at 75° C. After allowing cooling down, water was added, and the reaction mixture was extracted with ethyl acetate. The combined organic phases were washed with brine then dried with magnesium sulfate, concentrated in vacuo and purified by column chromatography to yield the title compound (2.3 g, 76%). MS (EI): 312.1 (M+).
Workup
- customthe temperature below 7.5° C
- temperatureAfter allowing cooling down
- extractionthe reaction mixture was extracted with ethyl acetate
- washThe combined organic phases were washed with brine
- dry with materialthen dried with magnesium sulfate
- concentrationconcentrated in vacuo
- custompurified by column chromatography
Sources & evidence
- ORD record
- ord-6a17939290a2498d8a220444d957ac8b
- Source dataset
- uspto-grants-2008_05
- Patent number
- US07375226B2
Reaction notes
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