Dimethylformamide → Ethyl 3-bromo-4-chloro-5-methyl-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrole-2-carboxylate
Reaction equation
[H-].[Na+].[Br:3][C:4]1[C:8]([Cl:9])=[C:7]([CH3:10])[NH:6][C:5]=1[C:11]([O:13][CH2:14][CH3:15])=[O:12].[CH3:16][Si:17]([CH:20](Cl)[CH2:21]C)([CH3:19])[CH3:18].CN([CH:27]=[O:28])C>>[Br:3][C:4]1[C:8]([Cl:9])=[C:7]([CH3:10])[N:6]([CH2:27][O:28][CH2:21][CH2:20][Si:17]([CH3:19])([CH3:18])[CH3:16])[C:5]=1[C:11]([O:13][CH2:14][CH3:15])=[O:12]Participants
5
Conditions
- Temperature
- 0 °C
Procedure
To a suspension of sodium hydride (76 mg, 3.16 mmol) in dry DMF (5 ml), solution of ethyl 3-bromo-4-chloro-5-methyl-1H-pyrrole-2-carboxylate (Intermediate 267, 420 mg, 1.58 mg) was added, the resulting mixture was stirred at 0° C. for 30 minutes until gas evolution seized. Trimethylsilyl-ethylmethyl chloride (315 mg, 1.89 mmol) was added drop wise and stirred over night while allowing the reaction mixture warmed up to room temperature slowly. The reaction was quenched with cold water, diluted with ether (20 ml), washed with water and brine, the organic layer was dried over anhydrous sodium sulfate, concentrated and purified by column chromatography (95% hexanes in ethyl acetate) to give the desired product as an oil (624 mg).
Workup
- additionwas added
- stirringstirred over night
- temperaturewarmed up to room temperature slowly
- customThe reaction was quenched with cold water
- additiondiluted with ether (20 ml)
- washwashed with water and brine
- dry with materialthe organic layer was dried over anhydrous sodium sulfate
- concentrationconcentrated
- custompurified by column chromatography (95% hexanes in ethyl acetate)
Sources & evidence
- ORD record
- ord-ec05b7c5c04242c4b08d91fc3082c862
- Source dataset
- uspto-grants-2013_03
- Patent number
- US08399489B2
Reaction notes
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