Hydrochloric Acid → HCID 21999001, compound

HRID 1976735Notes

Reaction equation

HRID 1976735 reaction equation
[F:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:12]3[C:13](=[O:31])[NH:14][C:15](=[O:30])[C:16]=3[C:17]3[C:25]4[C:20](=[CH:21][C:22]([N+:26]([O-])=O)=[CH:23][CH:24]=4)[N:19]([CH3:29])[CH:18]=3)=[CH:7][N:8]2[CH3:11])=[CH:4][CH:3]=1.Cl.O.NN>C(O)C.O1CCCC1.[Pd]>[NH2:26][C:22]1[CH:21]=[C:20]2[C:25]([C:17]([C:16]3[C:15](=[O:30])[NH:14][C:13](=[O:31])[C:12]=3[C:6]3[C:5]4[C:9](=[CH:10][C:2]([F:1])=[CH:3][CH:4]=4)[N:8]([CH3:11])[CH:7]=3)=[CH:18][N:19]2[CH3:29])=[CH:24][CH:23]=1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 24654Hydrazine hydrate (1:1)HCID 15513664HCID 15513664, compound

Product 1

HCID 21999001HCID 21999001, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 1.0 g (2.39 mmole) of 3-(6-fluoro-1-methyl-1H-indol-3-yl)-4-(1-methyl-6-nitro-1H-indol-3-yl)-pyrrole-2,5-dione in 20 ml of ethanol and 10 mL of tetrahydrofuran was added 0.55 g of 10% Pd/C and 0.54 mL of 5% hydrochloric acid. The mixture was cooled in an ice bath, and 0.54 mL (14.34 mmole) of hydrazine hydrate (85%) was added dropwise over 5 min. The reaction mixture was allowed to warm to room temp as it was stirred for two hours. The catalyst was removed by filtration over Celite. The filtrate was evaporated and the residue was crystallized from ethyl acetate/tetrahydrofuran/hexane to give 708 mg (76%) of )3-(6-amino-1-methyl-1H-indol-3-yl)-4-(6-fluoro-1-methyl-1H-indol-3-yl)-pyrrole-2,5-dione.

Workup

  1. temperatureThe mixture was cooled in an ice bath
  2. customThe catalyst was removed by filtration over Celite
  3. customThe filtrate was evaporated
  4. customthe residue was crystallized from ethyl acetate/tetrahydrofuran/hexane

Sources & evidence

ORD record
ord-dca4e1d38b27454ea236e3c17c41e079
Source dataset
uspto-grants-2001_05
Patent number
US06228877B1

Reaction notes

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