Sodium Bicarbonate → HCID 66887603, compound

HRID 2196667Notes

Reaction equation

HRID 2196667 reaction equation
[I:1][C:2]1[C:10]2[C:5](=[N:6][CH:7]=[C:8]([N+:11]([O-])=O)[CH:9]=2)[N:4]([S:14]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)(=[O:16])=[O:15])[CH:3]=1.C([O-])(O)=O.[Na+]>CCOC(C)=O>[I:1][C:2]1[C:10]2[C:5](=[N:6][CH:7]=[C:8]([NH2:11])[CH:9]=2)[N:4]([S:14]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)(=[O:16])=[O:15])[CH:3]=1

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 671558343-Iodo-5-nitro-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 66887603HCID 66887603, compoundYield 100.3%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

3-Iodo-5-nitro-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine (1.00 g, 2.33 mmol) and SnCl2 dihydrate (2.63 g, 11.7 mmol) in EtOAc (25 mL) were heated to 75° C. for 4 hours. The reaction mixture was cooled to room temperature, and saturated aqueous NaHCO3 (25 mL) was added. The resulting precipitate was filtered through celite. The layers were separated. The organic portion was washed with water, brine, dried over Na2SO4 and concentrated to give 3-iodo-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-5-amine (0.933 g, 100%) as a powder, which was used directly in the next step without further purification.

Workup

  1. filtrationThe resulting precipitate was filtered through celite
  2. customThe layers were separated
  3. washThe organic portion was washed with water, brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-8ae5395f742e4d7fbcdb1a503612f654
Source dataset
uspto-grants-2012_12
Patent number
US08338452B2

Reaction notes

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