Tris(furan-2-yl)phosphane → HCID 59749445, compound

HRID 747235

Reaction equation

HRID 747235 reaction equation
[Si:1]([O:8][CH2:9][CH:10]1[O:14][N:13]=[C:12]([C:15]2[CH:20]=[CH:19][C:18]([Sn](C)(C)C)=[CH:17][CH:16]=2)[CH2:11]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].I[C:26]1[CH:31]=[CH:30][C:29]([N:32]2[CH2:36][C@H:35]([CH2:37][N:38]3[CH:42]=[C:41]([CH3:43])[N:40]=[N:39]3)[O:34][C:33]2=[O:44])=[CH:28][CH:27]=1.O1C=CC=C1P(C1OC=CC=1)C1OC=CC=1>O1CCOCC1.[Pd].C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1>[Si:1]([O:8][CH2:9][CH:10]1[O:14][N:13]=[C:12]([C:15]2[CH:20]=[CH:19][C:18]([C:26]3[CH:31]=[CH:30][C:29]([N:32]4[CH2:36][C@H:35]([CH2:37][N:38]5[CH:42]=[C:41]([CH3:43])[N:40]=[N:39]5)[O:34][C:33]4=[O:44])=[CH:28][CH:27]=3)=[CH:17][CH:16]=2)[CH2:11]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 521585Tris(furan-2-yl)phosphaneHCID 597494295-({[tert-Butyl(dimethyl)silyl]oxy}methyl)-3-[4-(trimethylstannyl)phenyl]4,5-dihydroisoxazoleHCID 59749434(5R)-3-(4-Iodophenyl)-5-[(4-methyl-1H-1,2,3-triazol-1-yl)methyl]-1,3-oxazolidin-2-one

Product 1

HCID 59749445HCID 59749445, compoundYield 28.3%

Reagents, catalysts & solvents 2

HCID 44556509Tris(dibenzylideneacetone) palladiumCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

5-({[tert-Butyl(dimethyl)silyl]oxy}methyl)-3-[4-(trimethylstannyl)phenyl]4,5-dihydroisoxazole (0.70 g, 1.6 mmol), (5R)-3-(4-iodophenyl)-5-[(4-methyl-1H-1,2,3-triazol-1-yl)methyl]-1,3-oxazolidin-2-one (0.5 g, 1.29 mmol), tri-2-furyl phosphine (0.06 g, 0.26 mmol) and tris(dibenzylideneacetone)palladium (0) (0.12 g, 0.13 mmol) were dissolved in 1,4-dioxane (5 ml) and degassed three times. The mixture was then heated to 90° C. and stirred for 18 hr. LCMS indicated that the reaction was not yet complete, so it was cooled and an additional (0.12 g, 0.13 mmol) of tris(dibenzylidene acetone) palladium (0) was added, the mixture degassed and reheated to 110° C. for 3 hours, and 25° C. for 40 hours. The solution was concentrated in vacuo and purified by silica flash chromatography with 5-10% methanol in dichloromethane as eluent giving 0.2 g of the desired product as a yellow solid.

Workup

  1. customdegassed three times
  2. temperatureso it was cooled
  3. customthe mixture degassed
  4. waitreheated to 110° C. for 3 hours
  5. wait25° C. for 40 hours
  6. concentrationThe solution was concentrated in vacuo
  7. custompurified by silica flash chromatography with 5-10% methanol in dichloromethane as eluent

Sources & evidence

ORD record
ord-aa766d7d8b7b4900aa80758113d2bce9
Source dataset
uspto-grants-2008_07
Patent number
US07396847B2

Linked notes

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