Phosphine, tris(4-methoxyphenyl)- → HCID 10194990, compound

HRID 1268973Notes

Reaction equation

HRID 1268973 reaction equation
[O:1]=[S:2]1(=[O:31])[CH2:7][CH:6]=[C:5]([C:8]2[CH:13]=[CH:12][C:11]([N:14]3[CH2:18][C@H:17]([CH2:19][N:20]4[CH:24]=[C:23]([CH:25]=[C:26](Br)Br)[N:22]=[N:21]4)[O:16][C:15]3=[O:29])=[CH:10][C:9]=2[F:30])[CH2:4][CH2:3]1.[CH2:32]([Sn](CCCC)(CCCC)CCCC)[CH:33]=C.COC1C=CC(P(C2C=CC(OC)=CC=2)C2C=CC(OC)=CC=2)=CC=1.C(N(C(C)C)CC)(C)C>CN(C=O)C.C(OCC)(=O)C.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]>[O:1]=[S:2]1(=[O:31])[CH2:7][CH:6]=[C:5]([C:8]2[CH:13]=[CH:12][C:11]([N:14]3[CH2:18][C@H:17]([CH2:19][N:20]4[CH:24]=[C:23]([C:25]#[C:26][CH:32]=[CH2:33])[N:22]=[N:21]4)[O:16][C:15]3=[O:29])=[CH:10][C:9]=2[F:30])[CH2:4][CH2:3]1

Participants

8

Reactant 4

HCID 70071Phosphine, tris(4-methoxyphenyl)-HCID 81531DiisopropylethylamineHCID 90628AllyltributylstannaneHCID 10175195HCID 10175195, compound

Product 1

HCID 10194990HCID 10194990, compoundYield 14%

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

(5R)-3-[4-(1,1-Dioxo-3,6-dihydro-2H-thiopyran-4-yl)-3-fluorophenyl]-5-[4-(2,2-dibromoethenyl)-1,2,3-triazol-1-ylmethyl]oxazolidin-2-one (Example 25) (0.3 g, 0.52 mmol), allyl tributyl tin (160 μl, 0.55 mmol) and tris(4-methoxyphenyl)phosphine (28 mg, 0.08 mmol) were dissolved in DMF (2.5 ml). Diisopropylethyl amine (136 μl, 0.78 mmol) was added, the reaction mixture was flushed with argon and tris(dibenzylideneacetone)dipalladium (0) (15 mg, 0.01 mmol) was added. The mixture was heated to 80° C. for 10 hours under argon. It was diluted with ethyl acetate, washed with phosphate buffer (pH 7), saturated aqueous potassium fluoride solution and with water and dried over sodium sulfate. Chromatography on silica gel with chloroform/methanol (15:1) gave 32 mg (14%) of the title compound as a colourless solid.

Workup

  1. additionwas added
  2. washwashed with phosphate buffer (pH 7), saturated aqueous potassium fluoride solution and with water
  3. dry with materialdried over sodium sulfate

Sources & evidence

ORD record
ord-44f384bc19224f43a5893cff10b1a025
Source dataset
uspto-grants-2007_04
Patent number
US07199143B2

Reaction notes

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