Sodium Azide → 3-[5-(1,1-Difluoro-ethyl)-tetrazol-1-yl]-5-(5-methyl-pyridin-2-yl)-benzoic acid methyl ester

HRID 84756Notes

Reaction equation

HRID 84756 reaction equation
[CH3:1][O:2][C:3](=[O:24])[C:4]1[CH:9]=[C:8]([C:10]2[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][N:11]=2)[CH:7]=[C:6]([N:17]=[C:18](Cl)[C:19]([F:22])([F:21])[CH3:20])[CH:5]=1.[N-:25]=[N+:26]=[N-:27].[Na+]>C(#N)C>[CH3:1][O:2][C:3](=[O:24])[C:4]1[CH:9]=[C:8]([C:10]2[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][N:11]=2)[CH:7]=[C:6]([N:17]2[C:18]([C:19]([F:22])([F:21])[CH3:20])=[N:27][N:26]=[N:25]2)[CH:5]=1

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 866173893-(1-Chloro-2,2-difluoro-propylideneamino)-5-(5-methyl-pyridin-2-yl)-benzoic acid methyl ester

Product 1

HCID 666640383-[5-(1,1-Difluoro-ethyl)-tetrazol-1-yl]-5-(5-methyl-pyridin-2-yl)-benzoic acid methyl esterYield 97.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

3-(1-Chloro-2,2-difluoro-propylideneamino)-5-(5-methyl-pyridin-2-yl)-benzoic acid methyl ester (0.611 g, 1.732 mmol) and NaN3 (0.225 g, 3.464 mmol) were added to 10 mL acetonitrile, and the mixture was stirred at room temperature for 90 minutes. Solvent was removed under reduced pressure and the residue was partitioned between water and EtOAc. The combined organic layers were washed with water, dried (MgSO4), filtered and concentrated under reduced pressure to give 0.605 g of 3-[5-(1,1-Difluoro-ethyl)-tetrazol-1-yl]-5-(5-methyl-pyridin-2-yl)-benzoic acid methyl ester as a white powder, MS (M+H)=360.

Workup

  1. customSolvent was removed under reduced pressure
  2. customthe residue was partitioned between water and EtOAc
  3. washThe combined organic layers were washed with water
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-28dcaa3b3b244ba282cfe4cd142a51ae
Source dataset
uspto-grants-2014_09
Patent number
US08846945B2

Reaction notes

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