HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2059665Generated: October 26, 2026
Sodium Azide → 2-Chloro-6-methyl-4-(1-methyl-1H-tetrazol-5-yl)-pyridine
https://huagongshe.com/reaction/2059665
Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sodium Azide | HCID 33557 | — |
| Reactant | Trifluoromethanesulfonic anhydride | HCID 67749 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | 2-Chloro-6,N,N-trimethyl-isonicotinamide | HCID 56966855 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | 2-Chloro-6-methyl-4-(1-methyl-1H-tetrazol-5-yl)-pyridine | HCID 59534353 | 10.7% |
Reaction Steps
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).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08278302B2 |
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| Source dataset | uspto-grants-2012_10 |
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| ORD ID | ord-90003159414f4a2c916f0816e0eddf23 |
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| Source note | uspto-grants-2012_10 |
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