1,4-Cyclohexadiene → HCID 10226836, compound

HRID 427765Notes

Reaction equation

HRID 427765 reaction equation
C([O:8][P:9]([N:19]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[C:21]([C:28]2[C:29](=[O:47])[NH:30][C:31](=[O:46])[C:32]=2[C:33]2[C:41]3[C:36](=[CH:37][C:38]([N+:42]([O-:44])=[O:43])=[CH:39][CH:40]=3)[N:35]([CH3:45])[CH:34]=2)=[CH:20]1)(=[O:18])[O:10]CC1C=CC=CC=1)C1C=CC=CC=1.C1CC=CCC=1>C1COCC1.C(O)C.[Pd]>[CH3:45][N:35]1[C:36]2[C:41](=[CH:40][CH:39]=[C:38]([N+:42]([O-:44])=[O:43])[CH:37]=2)[C:33]([C:32]2[C:31](=[O:46])[NH:30][C:29](=[O:47])[C:28]=2[C:21]2[C:22]3[C:27](=[CH:26][CH:25]=[CH:24][CH:23]=3)[N:19]([P:9](=[O:8])([OH:18])[OH:10])[CH:20]=2)=[CH:34]1

Participants

5

Reactant 2

HCID 123431,4-CyclohexadieneHCID 70153794{3-[4-(1-methyl-6-nitro-1H-indol-3-yl)-2,5-dioxo-2,5-dihydro-1H-pyrrol-3-yl]-indol-1-yl}-phosphonic acid dibenzyl ester

Product 1

HCID 10226836HCID 10226836, compoundYield 55%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21873804Tetrahydrofuran ethanolSolvent

Conditions

Temperature
37.5 °C

Procedure

A solution of {3-[4-(1-methyl-6-nitro-1H-indol-3-yl)-2,5-dioxo-2,5-dihydro-1H-pyrrol-3-yl]-indol-1-yl}-phosphonic acid dibenzyl ester (50 mg, 0.08 mmol) (from step a) above) in a mixture of THF/ethanol (3 ml/6 ml) was treated with 10% Pd/C (75 mg) and 1,4-cyclohexadiene (0.5 ml) and warmed to 35-40° C. for 2 hr. The reaction was cooled, filtered through celite and evaporated to dryness. Crystals were obtained from THF/hexane to yielding 20 mg of {3-[4-(1-methyl-6-nitro-1H-indol-3-yl)-2,5-dioxo-2,5-dihydro-1H-pyrrol-3-yl]-indol-1-yl}-phosphonic acid. (Yield 55 %)

Workup

  1. temperatureThe reaction was cooled
  2. filtrationfiltered through celite
  3. customevaporated to dryness
  4. customCrystals were obtained from THF/hexane

Sources & evidence

ORD record
ord-a1ed75f4d1d649ed855f11ae6225ea71
Source dataset
uspto-grants-2001_11
Patent number
US06313143B1

Reaction notes

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