Sodium Hydroxide → 5-Chloro-3-methyl-3H-[1,2,3]triazolo[4,5-B]pyridine

HRID 873962Notes

Reaction equation

HRID 873962 reaction equation
[N:1]([O-])=O.[Na+].[Cl:5][C:6]1[N:11]=[C:10]([NH:12][CH3:13])[C:9]([NH2:14])=[CH:8][CH:7]=1.[OH-].[Na+]>Cl>[Cl:5][C:6]1[N:11]=[C:10]2[N:12]([CH3:13])[N:1]=[N:14][C:9]2=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 23668193Sodium NitriteHCID 249039426-Chloro-N2-methylpyridine-2,3-diamine

Product 1

HCID 846532705-Chloro-3-methyl-3H-[1,2,3]triazolo[4,5-B]pyridineYield 64%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
0 °C

Procedure

NaNO2 (350 mg, 5.08 mmol) was added to a stirred solution of 6-chloro-N2-methylpyridine-2,3-diamine (Step 102.2) (800 mg, 5.08 mmol) in 2N HCl (8 mL) at 0° C. and the resulting mixture was stirred for 10 min at 0° C. The reaction was basified with 2N NaOH and extracted with CH2Cl2. The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated under reduced pressure. The crude material was purified by silica gel column chromatography (50% EtOAc/hexane) to afford the title product (545 mg, 3.23 mmol, 64% yield) as beige solid. tR: 0.69 min (LC-MS 2); ESI-MS: 168/170 [M+H]+ (LC-MS 2); Rf=0.46 (50% EtOAc/hexane); 1H NMR (400 MHz, DMSO-d6) δ ppm 4.25 (s, 3H) 7.44-7.62 (m, 1H) 8.62 (d, J=8.6 Hz, 1H).

Workup

  1. extractionextracted with CH2Cl2
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe crude material was purified by silica gel column chromatography (50% EtOAc/hexane)

Sources & evidence

ORD record
ord-4cbf789cb1df4f09a17e8c3e7c1f3b1f
Source dataset
uspto-grants-2015_03
Patent number
US08975417B2

Reaction notes

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