Benzyl Bromide → HCID 5329783, compound

HRID 1871901Notes

Reaction equation

HRID 1871901 reaction equation
[OH:1][C:2]1[C:7]([C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[O:9])=[CH:6][N:5]=[C:4]2[NH:16][N:17]=[CH:18][C:3]=12.[CH2:19](Br)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>CO.C([O-])(O)=O.[Na+]>[C:20]1([CH2:19][O:1][C:2]2[C:7]([C:8]([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)=[O:9])=[CH:6][N:5]=[C:4]3[NH:16][N:17]=[CH:18][C:3]=23)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

5

Reactant 2

HCID 7498Benzyl BromideHCID 178519490HCID 178519490, compound

Product 1

HCID 5329783HCID 5329783, compoundYield 20%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a solution of [4-hydroxy-1H-pyrazolo[3,4-b]pyridin-5-yl]phenylmethanone (50 mg, 0.21 mmol) in methanol (1 mL) and saturated aqueous NaHCO3 solution (10 mL) was added benzyl bromide (0.027 mL, 0.23 mmol). The reaction mixture was stirred at room temperature for 16 h and extracted with CH2Cl2 (3×10 mL). The combined organic layers were dried (Na2SO4) and concentrated in vacuo to give an oil. The crude material was purified by flash chromatography (SiO2, 230-400 mesh, eluted with 1:19 MEOH/CH2Cl2) to afford the title compound (13 mg, 20%) as a white solid.

Workup

  1. extractionextracted with CH2Cl2 (3×10 mL)
  2. dry with materialThe combined organic layers were dried (Na2SO4)
  3. concentrationconcentrated in vacuo
  4. customto give an oil
  5. customThe crude material was purified by flash chromatography (SiO2, 230-400 mesh, eluted with 1:19 MEOH/CH2Cl2)

Sources & evidence

ORD record
ord-b93c7cffd4f34dcab454a66bd464d86c
Source dataset
uspto-grants-2000_08
Patent number
US06107305

Reaction notes

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