Dimethylformamide → methyl 4-(4-chlorophenyl)-1H-pyrrole-2-carboxylate

HRID 2420692Notes

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]=1

Participants

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 cone, 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, and cone, in vacuo
customto 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-df68e304a4aa45ad842f53808298ae6c
Source dataset: uspto-grants-2011_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07956049B2

Reaction notes

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