Sodium Cyanide → HCID 68513219, compound

HRID 1952354Notes

Reaction equation

HRID 1952354 reaction equation
Br[CH2:2][C:3]1[C:11]2[C:6](=[N:7][CH:8]=[CH:9][CH:10]=2)[N:5]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[N:4]=1.[C-:19]#[N:20].[Na+]>CN(C=O)C.O>[C:19]([CH2:2][C:3]1[C:11]2[C:6](=[N:7][CH:8]=[CH:9][CH:10]=2)[N:5]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[N:4]=1)#[N:20]

Participants

5

Reactant 2

HCID 8929Sodium CyanideHCID 10828872tert-Butyl 3-(bromomethyl)-1H-pyrazolo[3,4-b]pyridine-1-carboxylate

Product 1

HCID 68513219HCID 68513219, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of tert-butyl 3-(bromomethyl)-1H-pyrazolo[3,4-b]pyridine-1-carboxylate (5.18 g, 16.59 mmol) in DMF (30 mL) was added sodium cyanide (1.626 g, 33.2 mmol) and stirred at 25° C. for 4 hours. After this time, the mixture was diluted with water (300 mL) and extracted with ethyl acetate (3×300 mL). The extracts were combined and the resulting solid precipitate was filtered. The filtrate was dried over MgSO4, filtered and the solvent removed in vacuo. This residue was purified by chromatography using 120 g RediSep column and eluting with 0-100% EtOAc/CH2Cl2 gradient. The desired fractions were combined and evaporated in vacuo to provide the title compound. LRMS (M+1): 259.1.

Workup

  1. extractionextracted with ethyl acetate (3×300 mL)
  2. filtrationthe resulting solid precipitate was filtered
  3. dry with materialThe filtrate was dried over MgSO4
  4. filtrationfiltered
  5. customthe solvent removed in vacuo
  6. customThis residue was purified by chromatography
  7. washeluting with 0-100% EtOAc/CH2Cl2 gradient
  8. customevaporated in vacuo

Sources & evidence

ORD record
ord-b52e59dd1ffd44a79592224e061d6b09
Source dataset
uspto-grants-2013_03
Patent number
US08404856B2

Reaction notes

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