Triphenylarsine → HCID 10279442, compound

HRID 857377Notes

Reaction equation

HRID 857377 reaction equation
[Br:1][C:2]1[C:3]2[C:4]([S:19][C:20]3[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][CH:21]=3)=[C:5]3[CH:14]([CH2:15][C:16]([OH:18])=[O:17])[CH2:13][CH2:12][N:6]3[C:7]=2[CH:8]=[C:9](I)[CH:10]=1.C1([As](C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH3:46][N:47]1[CH:51]=[CH:50][CH:49]=[C:48]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]>[Br:1][C:2]1[C:3]2[C:4]([S:19][C:20]3[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][CH:21]=3)=[C:5]3[CH:14]([CH2:15][C:16]([OH:18])=[O:17])[CH2:13][CH2:12][N:6]3[C:7]=2[CH:8]=[C:9]([C:48]2[N:47]([CH3:46])[CH:51]=[CH:50][CH:49]=2)[CH:10]=1

Participants

6

Reactant 3

HCID 11773TriphenylarsineHCID 27693971-methyl-2-(tributylstannyl)-1H-pyrroleHCID 10209818HCID 10209818, compound

Product 1

HCID 10279442HCID 10279442, compound

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 6228DimethylformamideSolvent

Procedure

To a solution of (+/−)-methyl {8-bromo-9-[(4-chlorophenyl)thio]-6-iodo-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl}acetate (see Example 30, 145 mg, 0.25 mmol) in DMF (3 mL) were added tris(dibenzylideneacetone)dipalladium(0) (23 mg, 0.025 mmol), triphenyl arsine (31 mg, 0.1 mmol) and 1-methyl-2-(tributylstannyl)-1H-pyrrole (111 mg, 0.3 mmol). The mixture was degassed and stirred at r.t. for 2 hours. The reaction mixture was poured into 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 15% EtOAc/hexane to give methyle ester of the title compound which was hydrolyzed following the procedures described in Step 10 of Example 7.

Workup

  1. customThe mixture was degassed
  2. additionThe reaction mixture was poured into 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 15% EtOAc/hexane

Sources & evidence

ORD record
ord-b1d72c1893054d2a9dac10fa494257ac
Source dataset
uspto-grants-2006_12
Patent number
US07144913B2

Reaction notes

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