Sodium Azide → 2-Chloro-6-methyl-4-(1-methyl-1H-tetrazol-5-yl)-pyridine

HRID 2059665Notes

Reaction equation

HRID 2059665 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:10]=[C:11]([CH3:13])[N:12]=1)[C:5]([N:7](C)[CH3:8])=O.S(OS(C(F)(F)F)(=O)=O)(C(F)(F)F)(=O)=O.[N-:29]=[N+:30]=[N-:31].[Na+].C([O-])(O)=O.[Na+]>C(#N)C.C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([C:5]2[N:7]([CH3:8])[N:31]=[N:30][N:29]=2)[CH:10]=[C:11]([CH3:13])[N:12]=1

Participants

7

Reactant 4

HCID 33557Sodium AzideHCID 67749Trifluoromethanesulfonic anhydrideHCID 516892Sodium BicarbonateHCID 569668552-Chloro-6,N,N-trimethyl-isonicotinamide

Product 1

HCID 595343532-Chloro-6-methyl-4-(1-methyl-1H-tetrazol-5-yl)-pyridineYield 10.7%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
-10 °C

Procedure

To a solution of 2-Chloro-6,N,N-trimethyl-isonicotinamide (2.3 g) in acetonitrile (30 ml) at −15° C. was added DCM (20 ml) pre-cooled triflic anhydride (3 mL) dropwise. This was stirred for 10 min at −10° C. and then sodium azide (4.6 g) was added. This was allowed to warm to room temperature and after 2 h, the reaction was neutralised with a cold 5% NaHCO3(aq) solution and extracted with EtOAc. The organic layer was separated, dried and concentrated in vacuum. Flash chromatography (100:0 to 40:60 gradient cyclohexane:EtOAc) afforded the title compound (260 mg). Rt=1.21 min (method D).

Workup

  1. temperatureto warm to room temperature and after 2 h
  2. extractionextracted with EtOAc
  3. customThe organic layer was separated
  4. customdried
  5. concentrationconcentrated in vacuum

Sources & evidence

ORD record
ord-90003159414f4a2c916f0816e0eddf23
Source dataset
uspto-grants-2012_10
Patent number
US08278302B2

Reaction notes

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