Ethyl Acetate → HCID 178526795, compound

HRID 1943918Notes

Reaction equation

HRID 1943918 reaction equation
B(Br)(Br)Br.C([O:12][CH2:13][C:14]1[C:22]2[C:17](=[N:18][CH:19]=[C:20]([N+:23]([O-:25])=[O:24])[CH:21]=2)[NH:16][N:15]=1)C1C=CC=CC=1.C([O-])(O)=O.[Na+].C(OCC)(=O)C>ClCCl>[N+:23]([C:20]1[CH:21]=[C:22]2[C:14]([CH2:13][OH:12])=[N:15][NH:16][C:17]2=[N:18][CH:19]=1)([O-:25])=[O:24]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 178526796HCID 178526796, compound

Product 1

HCID 178526795HCID 178526795, compoundYield 87.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

BBr3 (7.4 mL, 7.4 mmol, 1M in heptane) was added to a solution of 3-(benzyloxymethyl)-5-nitro-1H-pyrazolo[3,4-b]pyridine (0.70 g, 2.46 mmol) in dichloromethane (25 mL) at −78° C., and the reaction mixture was stirred at this temperature for 1 hour. Saturated aqueous NaHCO3 was added, followed by addition of ethyl acetate. The layers were separated, and the aqueous layer extracted with ethyl acetate (2×). 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-1H-pyrazolo[3,4-b]pyridin-3-yl)methanol (417 mg, 87%), as a solid.

Workup

  1. customThe layers were separated
  2. extractionthe aqueous layer extracted with ethyl acetate (2×)
  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-640a39dfdbb047629c2d184117cb1f14
Source dataset
uspto-grants-2013_03
Patent number
US08394795B2

Reaction notes

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