Water → HCID 67155969, compound

HRID 2196714Notes

Reaction equation

HRID 2196714 reaction equation
[BH4-].[Na+].[N+:3]([C:6]1[CH:7]=[C:8]2[CH:14]=[C:13]([CH:15]=[O:16])[N:12]([S:17]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)(=[O:19])=[O:18])[C:9]2=[N:10][CH:11]=1)([O-:5])=[O:4].O.C(OCC)(=O)C>C1COCC1.CO>[N+:3]([C:6]1[CH:7]=[C:8]2[CH:14]=[C:13]([CH2:15][OH:16])[N:12]([S:17]([C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)(=[O:18])=[O:19])[C:9]2=[N:10][CH:11]=1)([O-:5])=[O:4]

Participants

7

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 4311764Sodium borohydrideHCID 73013588HCID 73013588, compound

Product 1

HCID 67155969HCID 67155969, compoundYield 42.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

NaBH4 (0.084 g, 2.21 mmol) was added to a solution of 5-nitro-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine-2-carbaldehyde (611 mg, 1.844 mmol) in THF (18.3 mL) and methanol (1.8 mL) at 0° C. The reaction mixture was stirred for 1 hour. It was then treated with water and ethyl acetate, and the layers were separated. The aqueous layer was extracted with ethyl acetate. The combined organic layers were dried with sodium sulfate, filtered and concentrated in vacuo. The crude product was purified by flash chromatography to afford (5-nitro-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-2-yl)methanol (0.26 g, 42% yield).

Workup

  1. customthe layers were separated
  2. extractionThe aqueous layer was extracted with ethyl acetate
  3. dry with materialThe combined organic layers were dried with sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified by flash chromatography

Sources & evidence

ORD record
ord-b1a9a7bf90884a6c9156e88498b44d30
Source dataset
uspto-grants-2012_12
Patent number
US08338452B2

Reaction notes

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