Tert-Butyl nitrite → HCID 57950691, compound

HRID 598908Notes

Reaction equation

HRID 598908 reaction equation
N(OC(C)(C)C)=O.[NH2:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[NH:14][N:13]=[CH:12]2.C[Si]([N:22]=[N+:23]=[N-])(C)C>CC#N>[N:8]([C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[NH:14][N:13]=[CH:12]2)=[N+:22]=[N-:23]

Participants

5

Reactant 3

HCID 10906Tert-Butyl nitriteHCID 78378AzidotrimethylsilaneHCID 880121H-Indazol-5-amine

Product 1

HCID 57950691HCID 57950691, compoundYield 76.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
0 °C

Procedure

Neat tert-butyl nitrite (670 μL, 5633 μmol) was added to a suspension of 5-aminoindazole (500 mg, 3755 μmol) (commercially available from VWR Chemical Catalog (Order Number AAAL06705-14)) in MeCN (7 mL) at 0° C. followed by dropwise addition of trimethylsilyl azide (598 μL 4506 μmol). The mixture was stirred at 0° C. for 5 minutes room temperature for 18 hours, and at 50° C. for 24 hours. The mixture was concentrated under reduced pressure, and the resulting brown residue was absorbed onto silica gel and purified by flash chromatography (silica gel, 2% to 6% MeOH/DCM) to provide 5-azido-1H-indazole (456 mg, 76%) as a golden solid. LCMS (API-ES) m/z: 160.1 (M+H+).

Workup

  1. waitat 50° C. for 24 hours
  2. concentrationThe mixture was concentrated under reduced pressure
  3. customthe resulting brown residue was absorbed onto silica gel
  4. custompurified by flash chromatography (silica gel, 2% to 6% MeOH/DCM)

Sources & evidence

ORD record
ord-6e8ae935926d42738ddfa75295028343
Source dataset
uspto-grants-2011_03
Patent number
US07897619B2

Reaction notes

Loading…