N-bromobutanimide → ethyl 5-bromo-1,4-dimethyl-1H-pyrrole-2-carboxylate
Reaction equation
[CH3:1][N:2]1[CH:6]=[C:5]([CH3:7])[CH:4]=[C:3]1[C:8]([O:10][CH2:11][CH3:12])=[O:9].[Br:13]N1C(=O)CCC1=O>C(Cl)(Cl)Cl>[Br:13][C:6]1[N:2]([CH3:1])[C:3]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:4][C:5]=1[CH3:7]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a solution of ethyl 1,4-dimethyl-1H-pyrrole-2-carboxylate (63 mg, 0.377 mmol) in CHCl3 (3.5 mL) at 0° C. was added N-bromosuccinimide (67.1 mg, 0.377 mmol). The reaction was stirred at 0° C. for 15 min. The reaction was warmed to room temperature and stirred overnight. The reaction mixture was filtered and the filtrate was concentrated in vacuo. The residue was purified by preparative TLC (1000 μm, hexanes/EtOAc (9:1)) to give ethyl 5-bromo-1,4-dimethyl-1H-pyrrole-2-carboxylate. LCMS calc.=245.0. found=245.9 (M+H)+. 1H NMR (500 MHz, CDCl3): δ 6.83 (s, 1H); 4.27 (q, J=7.1 Hz, 2H); 3.91 (s, 3H); 2.05-2.02 (m, 3H); 1.34 (t, J=7.1 Hz, 3H).
Workup
- temperatureThe reaction was warmed to room temperature
- stirringstirred overnight
- filtrationThe reaction mixture was filtered
- concentrationthe filtrate was concentrated in vacuo
- customThe residue was purified by preparative TLC (1000 μm, hexanes/EtOAc (9:1))
Sources & evidence
- ORD record
- ord-7fb169b1beb84f2d9e71975dec1c2979
- Source dataset
- uspto-grants-2015_12
- Patent number
- US09221834B2
Reaction notes
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