Dimethylformamide → methyl 4-(4-chlorophenyl)-1H-pyrrole-2-carboxylate
Reaction equation
CN(C=O)C.Br[C:7]1[CH:8]=[C:9]([C:12]([O:14][CH3:15])=[O:13])[NH:10][CH:11]=1.C([O-])([O-])=O.[Na+].[Na+].[Cl:22][C:23]1[CH:28]=[CH:27][C:26](B(O)O)=[CH:25][CH:24]=1>O.CCOC(C)=O>[Cl:22][C:23]1[CH:28]=[CH:27][C:26]([C:7]2[CH:8]=[C:9]([C:12]([O:14][CH3:15])=[O:13])[NH:10][CH:11]=2)=[CH:25][CH:24]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 110 °C
Procedure
To a stirred DMF solution (40 mL) containing methyl 4-bromo-1H-pyrrole-2-carboxylate (1.0 g, 4.9 mmol), commercially available from Bionet, and Pd(Ph3)4 (195 mg, 0.17 mmol) was added Na2CO3 (1.3 g, 12.52 mmol) (dissolved in minimum amount water) and 4-chlorophenyl boronic acid (0.85 g, 5.43 mmol) under Ar. The mixture was degassed with Ar prior to stirring overnight at 110° C. After cooling the reaction to RT, it was diluted with 10 mL of water and 200 mL of EtOAc. The aqueous layer was extracted with EtOAc (3×20 mL). The organic layers were combined, dried over Na2SO4, and conc. in vacuo to yield a brown oil. The oil was purified by column chromatography (silica gel, 0%-15% gradient elution with EtOAc/hexanes) to yield 288 mg (25%) of product as white solid. MS (ESI) 236 (M+H)+.
Workup
- customThe mixture was degassed with Ar
- temperatureAfter cooling
- customthe reaction to RT
- extractionThe aqueous layer was extracted with EtOAc (3×20 mL)
- dry with materialdried over Na2SO4
- customconc. in vacuo to yield a brown oil
- customThe oil was purified by column chromatography (silica gel, 0%-15% gradient elution with EtOAc/hexanes)
Sources & evidence
- ORD record
- ord-0ef8e4e781bc42ce83171e53095d8a54
- Source dataset
- uspto-grants-2009_06
- Patent number
- US07553836B2
Reaction notes
Loading…