Tris(furan-2-yl)phosphane → HCID 59749509, compound

HRID 747237Notes

Reaction equation

C[Sn](C)(C)[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH2:13][CH:12]([CH2:14][N:15]3[CH:19]=[CH:18][N:17]=[N:16]3)[O:11][N:10]=2)=[CH:5][CH:4]=1.[F:22][C:23]1[CH:24]=[C:25]([N:30]2[CH2:34][C@H:33]([CH2:35][NH:36][C:37](=[O:39])[CH3:38])[O:32][C:31]2=[O:40])[CH:26]=[CH:27][C:28]=1I.O1C=CC=C1P(C1OC=CC=1)C1OC=CC=1>O1CCOCC1>[F:22][C:23]1[CH:24]=[C:25]([N:30]2[CH2:34][C@H:33]([CH2:35][NH:36][C:37](=[O:39])[CH3:38])[O:32][C:31]2=[O:40])[CH:26]=[CH:27][C:28]=1[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH2:13][CH:12]([CH2:14][N:15]3[CH:19]=[CH:18][N:17]=[N:16]3)[O:11][N:10]=2)=[CH:5][CH:4]=1

Participants

Conditions

Temperature: 90 °C

Procedure

1-({3-[4-(Trimethylstannyl)phenyl]-4,5-dihydroisoxazol-5-yl}methyl)-1H-1,2,3-triazole (0.62 g, 1.58 mmol), N-{[(5S)-3-(3-fluoro-4-iodophenyl)-2-oxo-1,3-oxazolidin-5-yl]methyl}acetamide (0.5 g, 1.32 mmol) and tri-2-furylphosphine (0.08 g, 0.34 mmol) were dissolved in 1,4-dioxane (6 ml) and degassed three times. Tris(dibenzylideneacetone)palladium (0) (0.16 g, 0.18 mmol) was added and the solution was degassed three times. The solution was stirred and heated to 90° C. for 18 hours. The mixture was concentrated in vacuo and then purified by silica flash chromatography with 5-10% methanol in dichloromethane as eluent giving 0.20 g desired product.

Workup

customdegassed three times
customthe solution was degassed three times
concentrationThe mixture was concentrated in vacuo
custompurified by silica flash chromatography with 5-10% methanol in dichloromethane as eluent

Sources & evidence

ORD record: ord-394eb66c82444f6da4b2e60d56749ba5
Source dataset: uspto-grants-2008_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07396847B2

Reaction notes

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