Water → α-Methyl-5-nitro-1H-pyrrolo[2,3-b]pyridine-2-methanol

HRID 2196724Notes

Reaction equation

HRID 2196724 reaction equation
[BH4-].[Na+].[N+:3]([C:6]1[CH:7]=[C:8]2[CH:14]=[C:13]([C:15](=[O:17])[CH3:16])[NH:12][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]([CH:15]([OH:17])[CH3:16])[NH:12][C:9]2=[N:10][CH:11]=1)([O-:5])=[O:4]

Participants

7

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 4311764Sodium borohydrideHCID 67156057HCID 67156057, compound

Product 1

HCID 67156164α-Methyl-5-nitro-1H-pyrrolo[2,3-b]pyridine-2-methanolYield 42.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Sodium tetrahydroborate (0.15 g, 4.10 mmol) was added to a solution of 1-(5-nitro-1H-pyrrolo[2,3-b]pyridin-2-yl)ethanone (0.28 g, 1.37 mmol) in THF (8.7 mL) and methanol (0.90 mL) at 0° C., after which the reaction mixture was warmed up to room temperature and stirred for 1 hour. The reaction mixture was then treated with water and ethyl acetate, and the layers were separated. The aqueous layer was extracted once with ethyl acetate. The organic layers were dried with sodium sulfate, filtered and concentrated in vacuo. The crude material was purified by flash chromatography to afford 1-(5-nitro-1H-pyrrolo[2,3-b]pyridin-2-yl)ethanol (0.12 g, 41%).

Workup

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

Sources & evidence

ORD record
ord-e7093db72d2644fdaa7ac2b1df4d36a1
Source dataset
uspto-grants-2012_12
Patent number
US08338452B2

Reaction notes

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