Triphenylarsine → HCID 18175159, compound

HRID 395591Notes

Reaction equation

HRID 395591 reaction equation
Br[C:2]1[NH:3][C:4]2[C:9]([C:10]=1[CH2:11][CH2:12][CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:8][C:7]([Cl:19])=[CH:6][CH:5]=2.C[Sn](C)(C)[C:22]1[CH:27]=[CH:26][C:25]([N+:28]([O-:30])=[O:29])=[CH:24][CH:23]=1.C1([As](C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O1CCOCC1>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>[Cl:19][C:7]1[CH:8]=[C:9]2[C:4](=[CH:5][CH:6]=1)[NH:3][C:2]([C:22]1[CH:27]=[CH:26][C:25]([N+:28]([O-:30])=[O:29])=[CH:24][CH:23]=1)=[C:10]2[CH2:11][CH2:12][CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15]

Participants

7

Reactant 4

HCID 11773TriphenylarsineHCID 312751,4-DioxaneHCID 9971210Stannane, trimethyl(4-nitrophenyl)-HCID 18175122HCID 18175122, compound

Product 1

HCID 18175159HCID 18175159, compoundYield 31%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 200 mg (0.58.10−3 mol) of ethyl 2-bromo-5-chloro-1H-indole-3-butanoate, 498 mg (1.74.10−3 mol) of trimethyl(4-nitrophenyl)tin, 140 mg (0.46.10−3 mol) of triphenylarsine, 108 mg (0.12.10−3 mol) of tris(dibenzylideneacetone)dipalladium and 12 ml of dioxane is prepared and this reaction medium is heated at 50° C. for 6 days, with stirring. After cooling, 12 ml of water are added and the mixture is then extracted with ethyl ether. The organic phase is subsequently washed with water and then dried and concentrated under reduced pressure. The residue is purified by chromatography on silica gel using a petroleum ether/ethyl acetate mixture (85/15; v/v) as the eluent. The fractions containing the expected compound are purified again by reversed phase chromatography on C18-grafted silica using an acetonitrile/water mixture (7/3; v/v) as the eluent to give 70 mg of the expected compound in the form of a yellow paste (yield=31%).

Workup

  1. customis prepared
  2. temperatureAfter cooling
  3. extractionthe mixture is then extracted with ethyl ether
  4. washThe organic phase is subsequently washed with water
  5. customdried
  6. concentrationconcentrated under reduced pressure
  7. customThe residue is purified by chromatography on silica gel using a petroleum ether/ethyl acetate mixture (85/15; v/v) as the eluent
  8. additionThe fractions containing the expected compound
  9. customare purified again by reversed phase chromatography on C18-grafted silica using an acetonitrile/water mixture (7/3; v/v) as the eluent

Sources & evidence

ORD record
ord-bbbed2dd6e0c4b1e9388d6b2b1fe89d3
Source dataset
uspto-grants-2003_08
Patent number
US06605633B1

Reaction notes

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