Water → 1-ethyl-2-(4-methylphenyl)-5-nitro-1H-pyrrolo[2,3-b]pyridine

HRID 541064Notes

Reaction equation

HRID 541064 reaction equation
[CH3:1][C:2](C)([O-])C.[K+].[N+:7]([C:10]1[CH:11]=[C:12]([C:17]#[C:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:13]([NH2:16])=[N:14][CH:15]=1)([O-:9])=[O:8].I[CH2:26]C.O>CN(C=O)C.CCOC(C)=O>[CH2:1]([N:16]1[C:13]2=[N:14][CH:15]=[C:10]([N+:7]([O-:9])=[O:8])[CH:11]=[C:12]2[CH:17]=[C:18]1[C:19]1[CH:24]=[CH:23][C:22]([CH3:26])=[CH:21][CH:20]=1)[CH3:2]

Participants

7

Reactant 4

HCID 962WaterHCID 6340IodoethaneHCID 23665647Potassium tert-butoxideHCID 593229015-Nitro-3-(phenylethynyl)pyridin-2-amine

Product 1

HCID 672852781-ethyl-2-(4-methylphenyl)-5-nitro-1H-pyrrolo[2,3-b]pyridine

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of potassium ter-butoxide (0.41 g, 3.7 mmol) in anhydrous DMF (5 ml) a solution of 5-nitro-3-(phenylethynyl)pyridin-2-amine (0.70 g, 2.8 mmol), in DMF (25 ml) was added dropwise while stirring at room temperature. After 1.5 days, iodoethane (0.38 ml, 4.7 mmol) was added and the whole stirred for additional 1.5 days. To the reaction H2O (50 ml) and EtOAc (100 ml) were then added. The mixture was poured into a separatory funnel, the organic layer separated, the aqueous one thoroughly extracted with EtOAc (50 ml) and combined organic layers washed with brine (2×100 ml). The organic solvent was removed by evaporation under reduced pressure and the residue was purified by column chromatography on silica gel (Et2O/n-hexane, Et2O 10%→20%) to give 1-ethyl-2-(4-methylphenyl)-5-nitro-1H-pyrrolo[2,3-b]pyridine:

Workup

  1. stirringthe whole stirred for additional 1.5 days
  2. additionwere then added
  3. additionThe mixture was poured into a separatory funnel
  4. customthe organic layer separated
  5. extractionthe aqueous one thoroughly extracted with EtOAc (50 ml)
  6. washwashed with brine (2×100 ml)
  7. customThe organic solvent was removed by evaporation under reduced pressure
  8. customthe residue was purified by column chromatography on silica gel (Et2O/n-hexane, Et2O 10%→20%)

Sources & evidence

ORD record
ord-5ad3d8841c9647509a1651858f706d34
Source dataset
uspto-grants-2014_10
Patent number
US08871948B2

Reaction notes

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