Triphenylarsine → HCID 58760715, compound

HRID 857379Notes

Reaction equation

HRID 857379 reaction equation
[CH2:1]([C@H:8]1[CH2:12][O:11][C:10](=[O:13])[N:9]1[C:14](=[O:38])[CH2:15][CH:16]1[C:20]2=[C:21]([S:30][C:31]3[CH:36]=[CH:35][C:34]([Cl:37])=[CH:33][CH:32]=3)[C:22]3[C:23](Br)=[CH:24][C:25]([F:28])=[CH:26][C:27]=3[N:19]2[CH2:18][CH2:17]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1([As](C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH3:58][N:59]1[CH:63]=[CH:62][CH:61]=[C:60]1[Sn](CCCC)(CCCC)CCCC>CN(C=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]>[CH2:1]([C@H:8]1[CH2:12][O:11][C:10](=[O:13])[N:9]1[C:14](=[O:38])[CH2:15][CH:16]1[C:20]2=[C:21]([S:30][C:31]3[CH:36]=[CH:35][C:34]([Cl:37])=[CH:33][CH:32]=3)[C:22]3[C:23]([C:60]4[N:59]([CH3:58])[CH:63]=[CH:62][CH:61]=4)=[CH:24][C:25]([F:28])=[CH:26][C:27]=3[N:19]2[CH2:18][CH2:17]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 11773TriphenylarsineHCID 27693971-methyl-2-(tributylstannyl)-1H-pyrroleHCID 58760744HCID 58760744, compound

Product 1

HCID 58760715HCID 58760715, compoundYield 102.8%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of (4S)-4-benzyl-3-({8-bromo-9-[(4-chlorophenyl)thio]-6-fluoro-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl}acetyl)-1,3-oxazolidin-2-one (Example 7A, Step 3, 230 mg, 0.38 mmol) in DMF (4 mL) were added tris(dibenzylideneacetone)dipalladium(0) (37 mg, 0.04 mmol), triphenyl arsine (49 mg, 0.16 mmol) and 1-methyl-2-(tributylstannyl)-1H-pyrrole (211 mg, 0.57 mmol). The mixture was degassed and stirred at 90° C. for 4 hours. The reaction was poured in 1N HCl and extracted with EtOAc. The combined organic layers were washed with brine, dried over Na2SO4 and concentrated. The residue was purified by silica gel chromatography eluted with 20% EtOAc/toluene to give 240 mg of the title compound as an orange oil.

Workup

  1. customThe mixture was degassed
  2. additionThe reaction was poured in 1N HCl
  3. extractionextracted with EtOAc
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel chromatography
  8. washeluted with 20% EtOAc/toluene

Sources & evidence

ORD record
ord-08ba0b9666c64270ae10219f966df9f2
Source dataset
uspto-grants-2006_12
Patent number
US07144913B2

Reaction notes

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