Sodium Azide → HCID 178514578, compound

HRID 1952334Notes

Reaction equation

HRID 1952334 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(OC(C)(C)C)=O)[N:4]=1.[N-:19]=[N+:20]=[N-:21].[Na+]>CN(C=O)C.O>[N:19]([CH2:2][C:3]1[C:11]2[C:6](=[N:7][CH:8]=[CH:9][CH:10]=2)[NH:5][N:4]=1)=[N+:20]=[N-:21]

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 10828872tert-Butyl 3-(bromomethyl)-1H-pyrazolo[3,4-b]pyridine-1-carboxylate

Product 1

HCID 178514578HCID 178514578, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 250 mg (0.80 mmol) of tert-butyl 3-(bromomethyl)-1H-pyrazolo[3,4-b]pyridine-1-carboxylate (1-1) and sodium azide (55 mg; 0.85 mmol) in 1 mL anhydrous DMF was heated at 90° C. for 5 hours. The reaction was cooled, diluted with water, and extracted twice with 25 mL portions of EtOAc. The combined EtOAc extracts were washed with brine, dried (anhydrous MgSO4) and concentrated to give a dark oil. The oil was purified by reverse phase preparative HPLC on a Gilson apparatus to give the title compound as a tan solid. MS M+1=152.

Workup

  1. temperatureThe reaction was cooled
  2. extractionextracted twice with 25 mL portions of EtOAc
  3. washThe combined EtOAc extracts were washed with brine
  4. dry with materialdried (anhydrous MgSO4)
  5. concentrationconcentrated
  6. customto give a dark oil
  7. customThe oil was purified by reverse phase preparative HPLC on a Gilson apparatus

Sources & evidence

ORD record
ord-68379e0fb42a47008fe93a23eca5173e
Source dataset
uspto-grants-2013_03
Patent number
US08404856B2

Reaction notes

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