Sodium hydride → HCID 117778922, compound
Reaction equation
[CH3:1][C:2]1[NH:3][C:4]2[C:9]([C:10]=1[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])=[CH:8][CH:7]=[CH:6][CH:5]=2.[H-].[Na+].[CH3:20][CH:21]([CH3:26])[CH2:22][C:23](Cl)=[O:24]>CN(C)C=O>[CH3:1][C:2]1[N:3]([C:23](=[O:24])[CH2:22][CH:21]([CH3:26])[CH3:20])[C:4]2[C:9]([C:10]=1[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])=[CH:8][CH:7]=[CH:6][CH:5]=2Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a solution of tert-butyl 2-methyl-1H-indole-3-carboxylate (300 mg, 1.30 mmol) in N,N-dimethylformamide (10 mL) was added sodium hydride (103.76 mg, 2.59 mmol, 60%). The mixture was stirred at 0° C. for 30 minutes. Then 3-methylbutanoyl chloride (234.60 mg, 1.95 mmol) was added at 0° C. and the mixture was stirred at room temperature (25° C.) for 2 hours. The mixture was cooled with ice, quenched with water (5 mL), diluted with ethyl acetate (20 mL), washed with brine (20 mL), extracted with ethyl acetate three times (20 mL×3), then dried over sodium sulfate. After concentration, the residue was purified by column on silica gel (0%-5% PE/EA) to afford the title compound (200 mg, yield: 48.89%).
Workup
- stirringthe mixture was stirred at room temperature (25° C.) for 2 hours
- temperatureThe mixture was cooled with ice
- customquenched with water (5 mL)
- additiondiluted with ethyl acetate (20 mL)
- washwashed with brine (20 mL)
- extractionextracted with ethyl acetate three times (20 mL×3)
- dry with materialdried over sodium sulfate
- concentrationAfter concentration
- customthe residue was purified by column on silica gel (0%-5% PE/EA)
Sources & evidence
- ORD record
- ord-5b1b97ea442c4d99953f4239a75fa2a5
- Source dataset
- uspto-grants-2015_07
- Patent number
- US09085583B2
Reaction notes
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