Pyrrole → methyl 4-[[3-(1H-pyrrol-1-yl)phenyl]methoxy]benzenepropanoate

HRID 2422225Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]([CH2:8][O:9][C:10]2[CH:15]=[CH:14][C:13]([CH2:16][CH2:17][C:18]([O:20][CH3:21])=[O:19])=[CH:12][CH:11]=2)[CH:5]=[CH:6][CH:7]=1.[NH:22]1[CH:26]=[CH:25][CH:24]=[CH:23]1.C(P(C(C)(C)C)C(C)(C)C)(C)(C)C.C(=O)([O-])[O-].[Cs+].[Cs+]>C1(C)C=CC=CC=1.O>[N:22]1([C:2]2[CH:3]=[C:4]([CH2:8][O:9][C:10]3[CH:15]=[CH:14][C:13]([CH2:16][CH2:17][C:18]([O:20][CH3:21])=[O:19])=[CH:12][CH:11]=3)[CH:5]=[CH:6][CH:7]=2)[CH:26]=[CH:25][CH:24]=[CH:23]1

Participants

Conditions

Temperature: 100 °C

Procedure

Methyl 4-[(3-bromophenyl)methoxy]benzenepropanoate (0.80 g, 2.3 mmol), pyrrole (0.17 g, 2.5 mmol), tri-tert-butylphosphine (19 mg, 0.092 mmol) and cesium carbonate (1.3 g, 3.9 mmol) were dissolved in toluene (25 mL) and, after argon substitution, tris(dibenzylidenacetone)dipalladium(0) (84 mg, 0.092 mmol) was added. The reaction mixture was heated under an argon atmosphere at 100° C. for 18 hrs. The reaction mixture was cooled, water was added to the reaction mixture and the mixture was extracted with ethyl acetate. The extract was washed with water, dried and concentrated. The residue was purified by silica gel column chromatography (ethyl acetate/hexane=15:1) to give the title compound (56 mg, yield 7%) as a yellow powder.

Workup

temperatureThe reaction mixture was cooled
extractionthe mixture was extracted with ethyl acetate
washThe extract was washed with water
customdried
concentrationconcentrated
customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane=15:1)

Sources & evidence

ORD record: ord-138b1a99a29c44548c78302d5d701246
Source dataset: uspto-grants-2011_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07960369B2

Reaction notes

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