Ethyl Acetate → HCID 10069251, compound

HRID 1976733Notes

Reaction equation

HRID 1976733 reaction equation
[C:1]([C:3]1[CH:11]=[C:10]2[C:6]([C:7]([C:13]3[C:14](=[O:32])[NH:15][C:16](=[O:31])[C:17]=3[C:18]3[C:26]4[C:21](=[CH:22][C:23]([N+:27]([O-])=O)=[CH:24][CH:25]=4)[N:20]([CH3:30])[CH:19]=3)=[CH:8][N:9]2[CH3:12])=[CH:5][CH:4]=1)#[N:2].O.O.[Sn](Cl)Cl.C(OCC)(=O)C.C(=O)(O)[O-].[Na+]>C(O)C>[NH2:27][C:23]1[CH:22]=[C:21]2[C:26]([C:18]([C:17]3[C:16](=[O:31])[NH:15][C:14](=[O:32])[C:13]=3[C:7]3[C:6]4[C:10](=[CH:11][C:3]([C:1]#[N:2])=[CH:4][CH:5]=4)[N:9]([CH3:12])[CH:8]=3)=[CH:19][N:20]2[CH3:30])=[CH:25][CH:24]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 61436Stannous chloride dihydrateHCID 516892Sodium BicarbonateHCID 15513668HCID 15513668, compound

Product 1

HCID 10069251HCID 10069251, compoundYield 78.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3-(6-cyano-1-methyl-1H-indol-3-yl)-4-(1-methyl-6-nitro-1H-indol-3-yl)-pyrrole-2,5-dione (9.0 g, 21 mmole) was suspended in ethanol (1.8 L) and treated with tin (II) chloride dihydrate (35 g, 156 mmole). This was mechanically stirred for 16 h at reflux. The reaction was cooled and reduced in volume to 1L. This was poured into a mixture of ethyl acetate (2 L) and saturated sodium bicarbonate solution (1 L) and well mixed. The organic layer was decanted and washed with saturated sodium bicarbonate solution, dried over magnesium sulfate, filtered, evaporated, and then purified by flash column chromatography (ethyl acetate). The product was further purified by crystalization from tetrahydrofuran/hexane to provide 6.5 g of 3-[4-(6-amino-1-methyl-1H-indol-3-yl)-2,5-dioxo-2,5-dihydro-1H-pyrrol-3-yl]-1-methyl-1H-indole-6-carbonitrile; mp 255-260° C.

Workup

  1. temperatureat reflux
  2. temperatureThe reaction was cooled
  3. additionwell mixed
  4. customThe organic layer was decanted
  5. washwashed with saturated sodium bicarbonate solution
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. customevaporated
  9. custompurified by flash column chromatography (ethyl acetate)
  10. customThe product was further purified by crystalization from tetrahydrofuran/hexane

Sources & evidence

ORD record
ord-0b3a4f94f2d649e892aca4038471b1a2
Source dataset
uspto-grants-2001_05
Patent number
US06228877B1

Reaction notes

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