Reaction #1509598

Reaction equation

NaHCO3

2-Chloro-6,N,N-trimethyl-isonicotinamide

triflic anhydride

sodium azide

→

title compound

Yield 10.7%

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

Yield 10.7%

Solvents

acetonitrile

DCM

Conditions

Workup

1. 1
   Temperatureto warm to room temperature and after 2 h
2. 2
   Extractionextracted with EtOAc
3. 3
   OtherThe organic layer was separated
4. 4
   Otherdried
5. 5
   Concentrationconcentrated in vacuum

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).

Source