Sodium Azide → HCID 86609940, compound

HRID 930570Notes

Reaction equation

HRID 930570 reaction equation
[CH2:1]([O:3][C:4](=[O:17])[CH2:5][N:6]1[C:10]2=[N:11][CH:12]=[CH:13][CH:14]=[C:9]2[C:8](CBr)=[N:7]1)[CH3:2].[N-:18]=[N+:19]=[N-:20].[Na+]>CN(C=O)C.CCOC(C)=O>[CH2:1]([O:3][C:4](=[O:17])[CH2:5][N:6]1[C:10]2=[N:11][CH:12]=[CH:13][CH:14]=[C:9]2[C:8]([N:18]=[N+:19]=[N-:20])=[N:7]1)[CH3:2]

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 57642772Ethyl [3-(bromomethyl)-1H-pyrazolo[3,4-b]pyridin-1-yl]acetate

Product 1

HCID 86609940HCID 86609940, compoundYield 109.8%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of (3-(bromomethyl)-pyrazolo[3,4-b]pyridine-1-yl)acetic acid ethyl ester (0.5 mmol, 1 eq.) and sodium azide (1 mmol, 2 eq.) in 1 mL of DMF was heated at 80° C. for 1 h. The resultant mixture was cooled to rt, diluted with 150 mL of EtOAc, washed with water (40 mL×3), brine, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The solvent was removed in vacuo to provide 135.2 mg desired product: HPLC retention time=1.84 minutes (Agilent Zorbax SB-C18, 2.1×50 mm, 5μ, 35° C.) using 1 ml/min flow rate, a 2.5 minute gradient of 20% to 100% B with a 1.1 minute wash at 100% B (A=0.1% formic acid/5% acetonitrile/94.9% water, B=0.1% formic acid/5% water/94.9% acetonitrile); MS (ES) M+H expect=261.1. found=261.4.

Workup

  1. washwashed with water (40 mL×3), brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-66d15eccf71446cdbd056ca85eb7c703
Source dataset
uspto-grants-2016_03
Patent number
US09296740B2

Reaction notes

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