methyl 2-chloro-5-(2-fluorophenyl)-4-methyl-1H-pyrrole-3-carboxylate → Methyl 5-(2-fluorophenyl)-4-methyl-1H-pyrrole-3-carboxylate
Reaction equation
Cl[C:2]1[NH:3][C:4]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[F:18])=[C:5]([CH3:11])[C:6]=1[C:7]([O:9][CH3:10])=[O:8]>CO.[C].[Pd]>[F:18][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=1[C:4]1[NH:3][CH:2]=[C:6]([C:7]([O:9][CH3:10])=[O:8])[C:5]=1[CH3:11]Participants
Procedure
To a solution of methyl 2-chloro-5-(2-fluorophenyl)-4-methyl-1H-pyrrole-3-carboxylate (10.2 g) in methanol (200 mL) was added 10% palladium carbon (50% containing water, 1.28 g), and the mixture was stirred under a hydrogen atmosphere at room temperature for 20 hr. The reaction mixture was filtered, and the filtrate was concentrated under reduced pressure. A saturated aqueous sodium hydrogencarbonate solution (100 mL) was added to the residue, and the mixture was extracted with ethyl acetate. The extract was washed with saturated aqueous sodium hydrogencarbonate solution, water and saturated brine, dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. Recrystallization of the residue from ethyl acetate-hexane gave the title compound as white crystals (yield 6.70 g, 76%).
Workup
- filtrationThe reaction mixture was filtered
- concentrationthe filtrate was concentrated under reduced pressure
- additionA saturated aqueous sodium hydrogencarbonate solution (100 mL) was added to the residue
- extractionthe mixture was extracted with ethyl acetate
- washThe extract was washed with saturated aqueous sodium hydrogencarbonate solution, water and saturated brine
- dry with materialdried over anhydrous sodium sulfate
- filtrationfiltered
- concentrationconcentrated under reduced pressure
- customRecrystallization of the residue from ethyl acetate-hexane
Sources & evidence
- ORD record
- ord-a4bf81a696ae4f30a6741154aa83f169
- Source dataset
- uspto-grants-2012_10
- Patent number
- US08299261B2
Reaction notes
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