Water → HCID 86729992, compound

HRID 2199767Notes

Reaction equation

HRID 2199767 reaction equation
[CH3:1][N:2]1[N:6]=[N:5][C:4]([NH2:7])=[N:3]1.Cl[C:9]1[CH:14]=[CH:13][C:12]([Br:15])=[CH:11][N:10]=1.CC([O-])(C)C.[K+].O>C1COCC1>[Br:15][C:12]1[CH:13]=[CH:14][C:9]([NH:7][C:4]2[N:5]=[N:6][N:2]([CH3:1])[N:3]=2)=[N:10][CH:11]=1

Participants

6

Reactant 4

HCID 962WaterHCID 1386772-methyl-2H-1,2,3,4-tetrazol-5-amineHCID 27344145-Bromo-2-chloropyridineHCID 23665647Potassium tert-butoxide

Product 1

HCID 86729992HCID 86729992, compoundYield 1.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-methyl-2H-tetrazole-5-amine (7.7 g, 78 mmol), 2-chloro-5-bromopyridine (10 g, 52 mmol), and potassium tert-butylate (11.6 g, 104 mmol) were dissolved in 100 mL THF, heated under reflux and reacted for 12 h. Water was added, extracted with ethyl acetate, and the organic phase was dried, concentrated, and the solid was separated by a silica gel column (dichloromethane:methanol=100:1) to obtain 5-bromo-N-(2-methyl-2H-tetrazol-5-yl)pyridine-2-amine 200 mg, at a yield of 1.5%.

Workup

  1. temperatureheated
  2. temperatureunder reflux
  3. customreacted for 12 h
  4. extractionextracted with ethyl acetate
  5. customthe organic phase was dried
  6. concentrationconcentrated
  7. customthe solid was separated by a silica gel column (dichloromethane:methanol=100:1)

Sources & evidence

ORD record
ord-fdb8d23ed5c4422cb1d7394e46bd77ad
Source dataset
uspto-grants-2016_06
Patent number
US09359344B2

Reaction notes

Loading…