Water → HCID 67155969, compound

HRID 2196733Notes

Reaction equation

HRID 2196733 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 65%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-40 °C

Procedure

Sodium tetrahydroborate (0.069 g, 1.81 mmol) was added to a solution of 5-nitro-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine-2-carbaldehyde (200 mg, 0.60 mmol) in THF (3.8 mL) and methanol (0.4 mL) at −40° C. The mixture was stirred at −40° C. for 30 minutes. 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 (5-nitro-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-2-yl)methanol (0.13 g, 65%).

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-ee7d495fbdc24546a23e31137c79c4a0
Source dataset
uspto-grants-2012_12
Patent number
US08338452B2

Reaction notes

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