Water → HCID 86653264, compound

HRID 2196732Notes

Reaction equation

HRID 2196732 reaction equation
[OH-].[Na+].[C:3]([C:5]1[N:16](S(C2C=CC=CC=2)(=O)=O)[C:8]2=[N:9][CH:10]=[C:11]([N+:13]([O-:15])=[O:14])[CH:12]=[C:7]2[CH:6]=1)#[CH:4].O.C(OCC)(=O)C>C1COCC1>[C:3]([C:5]1[NH:16][C:8]2=[N:9][CH:10]=[C:11]([N+:13]([O-:15])=[O:14])[CH:12]=[C:7]2[CH:6]=1)#[CH:4]

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 73013533HCID 73013533, compound

Product 1

HCID 86653264HCID 86653264, compoundYield 106.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

Sodium hydroxide (0.39 mL, 0.39 mmol, 1M in water) was added to a solution of 2-ethynyl-5-nitro-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine (0.032 g, 0.10 mmol) in THF (0.5 mL). The reaction mixture was heated at 60° C. for 90 minutes. The reaction mixture was then cooled down and treated with water and ethyl acetate. The layers were then separated. The aqueous layer was extracted once with ethyl acetate. The organic layers were dried over sodium sulfate, filtered, and evaporated to afford 2-ethynyl-5-nitro-1H-pyrrolo[2,3-b]pyridine (0.02 g, quantitative yield).

Workup

  1. temperatureThe reaction mixture was then cooled down
  2. customThe layers were then separated
  3. extractionThe aqueous layer was extracted once with ethyl acetate
  4. dry with materialThe organic layers were dried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-e9ec678bb643486ab366328e409ce368
Source dataset
uspto-grants-2012_12
Patent number
US08338452B2

Reaction notes

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