Tris(furan-2-yl)phosphane → HCID 58044954, compound

HRID 423192Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:15]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:14]3[C:13]([C:22]4[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=4)=[N:12][NH:11][C:10]=3[C:9]2=[O:30])=[CH:4][CH:3]=1.[O:31]1[CH:35]=[CH:34][NH:33]N1[Sn](CCCC)(CCCC)CCCC.O1C=CC=[C:50]1P(C1OC=CC=1)C1OC=CC=1>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O1CCOCC1>[CH3:29][O:28][C:25]1[CH:24]=[CH:23][C:22]([C:13]2[C:14]3[CH:15]([C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=4)[N:8]([C:5]4[CH:6]=[CH:7][C:2]([C:50]5[O:31][CH:35]=[CH:34][N:33]=5)=[CH:3][CH:4]=4)[C:9](=[O:30])[C:10]=3[NH:11][N:12]=2)=[CH:27][CH:26]=1

Participants

Conditions

Temperature: 130 °C

Procedure

A mixture of 5-(4-bromophenyl)-3-(4-methoxyphenyl)-4-phenyl-4,5-dihydro-1H-pyrrolo[3,4-c]pyrazol-6-one (0.138 g, 0.3 mmol), oxadiazol-2-yl tributyltin (0.134 g, 0.37 mmol), tris(2-furyl)phosphine (0.014 g, 0.06 mmol), tris(dibenzylideneacetone)dipalladium(0) (0.027 g, 0.03 mmol) and dioxane (1.5 mL) was stirred at 130° C. under microwave radiation for 75 min. The reaction mixture was purified by silica gel column chromatography (ethyl acetate/n-hexane). The fraction was concentrated under reduced pressure and the precipitate was collected by filtration to give 3-(4-methoxyphenyl)-5-(4-oxazol-2-ylphenyl)-4-phenyl-4,5-dihydro-1H-pyrrolo[3,4-c]pyrazol-6-one (12 mg, 10%) as colorless crystals.

Workup

customThe reaction mixture was purified by silica gel column chromatography (ethyl acetate/n-hexane)
concentrationThe fraction was concentrated under reduced pressure
filtrationthe precipitate was collected by filtration

Sources & evidence

ORD record: ord-082d9298895d4d0697814652c3ebfc03
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08101644B2

Reaction notes

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