Sodium Hydroxide → 6-bromo-3-methyl-3H-[1,2,3]triazolo[4,5-b]pyridine

HRID 445627Notes

Reaction equation

HRID 445627 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([NH2:10])[C:5]([NH:8][CH3:9])=[N:6][CH:7]=1.[N:11]([O-])=O.[Na+].[OH-].[Na+]>Cl.O>[Br:1][C:2]1[CH:3]=[C:4]2[N:10]=[N:11][N:8]([CH3:9])[C:5]2=[N:6][CH:7]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 151940325-Bromo-N2-methylpyridine-2,3-diamineHCID 23668193Sodium Nitrite

Product 1

HCID 596198246-bromo-3-methyl-3H-[1,2,3]triazolo[4,5-b]pyridine

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 5-bromo-N*2*-methyl-pyridine-2,3-diamine (Stage 67.1.4, 1.2 g, 5.94 mmol) in 2 M aqueous HCl (70 ml) cooled with an ice-bath was added a solution of sodium nitrite (Fluka, Buchs, Switzerland, 492 mg, 7.13 mmol) in water (10 ml). The reaction mixture was stirred at 0° C. for 1 h and at rt for 75 min then basified with 2 M aqueous NaOH (75 ml) and extracted with EtOAc. The organic layer was washed with brine, dried over Na2SO4, filtered and evaporated. The crude product was dry loaded on silica gel and purified by MPLC (heptane/EtOAc 0%-30%) to give the title compound as a blue solid. (HPLC: tR 2.46 min (Method A); M+H=213, 215 MS-ES).

Workup

  1. extractionextracted with EtOAc
  2. washThe organic layer was washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customevaporated
  6. dry with materialThe crude product was dry
  7. custompurified by MPLC (heptane/EtOAc 0%-30%)

Sources & evidence

ORD record
ord-dc27f67d56ed4eb587b5720a1cd44478
Source dataset
uspto-grants-2013_07
Patent number
US08476294B2

Reaction notes

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