ethyl 2-chloro-5-(2,6-difluorophenyl)-1H-pyrrole-3-carboxylate → ethyl 5-(2,6-difluorophenyl)-1H-pyrrole-3-carboxylate

HRID 1782279Notes

Reaction equation

Cl[C:2]1[NH:3][C:4]([C:12]2[C:17]([F:18])=[CH:16][CH:15]=[CH:14][C:13]=2[F:19])=[CH:5][C:6]=1[C:7]([O:9][CH2:10][CH3:11])=[O:8]>C(O)C.[C].[Pd]>[F:19][C:13]1[CH:14]=[CH:15][CH:16]=[C:17]([F:18])[C:12]=1[C:4]1[NH:3][CH:2]=[C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH:5]=1

Participants

Conditions

Temperature: 40 °C

Procedure

To a solution of ethyl 2-chloro-5-(2,6-difluorophenyl)-1H-pyrrole-3-carboxylate (9.82 g) in ethanol (200 mL) was added 10% palladium carbon (50% containing water, 4.91 g), and the mixture was stirred under a hydrogen atmosphere at 40° C. for 72 hr. The reaction mixture was filtered, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=4:1) to give the title compound as colorless crystals (yield 3.80 g, 24%).

Workup

filtrationThe reaction mixture was filtered
concentrationthe filtrate was concentrated under reduced pressure
customThe residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=4:1)

Sources & evidence

ORD record: ord-220ec73cbe7346479395b32bd15ef6e2
Source dataset: uspto-grants-2009_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07498337B2

Reaction notes

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