Sodium Azide → HCID 22050870, compound

HRID 1866965Notes

Reaction equation

HRID 1866965 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].[Br:5][C:6]1[C:7](=[O:21])[N:8]([CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([F:20])[CH:15]=2)[CH:9]=[CH:10][C:11]=1Br>CN(C)C=O>[N:1]([C:11]1[CH:10]=[CH:9][N:8]([CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([F:20])[CH:15]=2)[C:7](=[O:21])[C:6]=1[Br:5])=[N+:2]=[N-:3]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 22050873HCID 22050873, compound

Product 1

HCID 22050870HCID 22050870, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
60 °C

Procedure

Sodium azide (1.08 g, 16.62 mmol) was suspended in N,N-dimethylformamide (10 mL) and a stock solution of 3,4-dibromo-1-(3-fluorobenzyl)pyridin-2(1H)-one (from step 1) in N,N-dimethylformamide (33.0 mL, 0.33 M) was added and the resulting mixture was heated to 60° C. for 4 hours. Ice water (30 mL) was added and the aqueous layer was extracted with ethyl acetate (4×50 mL). The combined organics were washed with H2O (3×50 mL), brine (2×25 mL), dried over MgSO4, concentrated, and subjected to chromatography (silica gel, ethyl acetate with 10% methanol/hexane) to afford an off-white solid (3.50 g, 98%).

Workup

  1. extractionthe aqueous layer was extracted with ethyl acetate (4×50 mL)
  2. washThe combined organics were washed with H2O (3×50 mL), brine (2×25 mL)
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-31671c41bc8746b5b28d1872b6538670
Source dataset
uspto-grants-2009_12
Patent number
US07629363B2

Reaction notes

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