Sodium Azide → 2-(1-Azidoethyl)-3-(3,5-difluorophenyl)pyrazolo[1,5-a]pyridine

HRID 408804Notes

Reaction equation

HRID 408804 reaction equation
Br[CH:2]([C:4]1[C:12]([C:13]2[CH:18]=[C:17]([F:19])[CH:16]=[C:15]([F:20])[CH:14]=2)=[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][N:6]2[N:5]=1)[CH3:3].[N-:21]=[N+:22]=[N-:23].[Na+]>CN(C)C=O.C(OCC)(=O)C>[N:21]([CH:2]([C:4]1[C:12]([C:13]2[CH:18]=[C:17]([F:19])[CH:16]=[C:15]([F:20])[CH:14]=2)=[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][N:6]2[N:5]=1)[CH3:3])=[N+:22]=[N-:23]

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 583793362-(1-Bromoethyl)-3-(3,5-difluorophenyl)pyrazolo[1,5-a]pyridine

Product 1

HCID 583793422-(1-Azidoethyl)-3-(3,5-difluorophenyl)pyrazolo[1,5-a]pyridineYield 73%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

2-(1-Bromoethyl)-3-(3,5-difluorophenyl)pyrazolo[1,5-a]pyridine (0.63 g, 1.9 mmol) and sodium azide (0.12 g, 1.9 mmol) were stirred in N,N-dimethylformamide (20 mL) for 1 hour at 20° C. The mixture was diluted with ethyl acetate, washed with water, dried over magnesium sulfate, filtered, concentrated and purified on silica gel with ethyl acetate in hexanes (0-35%) to give the desired compound (0.41 g, 73%). LCMS for C15H12F2N5 (M+H)+: m/z=299.9. 1H NMR (300 MHz, DMSO-d6): δ 8.80 (m, 1H), 7.72 (m, 1H), 7.38 (m, 1H), 7.22 (m, 3H), 7.02 (m, 1H), 4.92 (m, 1H), 1.62 (m, 3H).

Workup

  1. washwashed with water
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. custompurified on silica gel with ethyl acetate in hexanes (0-35%)

Sources & evidence

ORD record
ord-38c03bcf3c4e43fa991a7c44415e59fc
Source dataset
uspto-grants-2014_06
Patent number
US08759359B2

Reaction notes

Loading…