Azidotrimethylsilane → HCID 89996213, compound

HRID 1480871Notes

Reaction equation

HRID 1480871 reaction equation
C[Si]([N:5]=[N+:6]=[N-:7])(C)C.[C:8]([C:10]1[N:15]=[C:14]([O:16][CH3:17])[C:13]([N+:18]([O-:20])=[O:19])=[CH:12][CH:11]=1)#[CH:9]>C1(C)C=CC=CC=1.O>[CH3:17][O:16][C:14]1[C:13]([N+:18]([O-:20])=[O:19])=[CH:12][CH:11]=[C:10]([C:8]2[CH:9]=[N:7][NH:6][N:5]=2)[N:15]=1

Participants

5

Reactant 2

HCID 78378AzidotrimethylsilaneHCID 89996215HCID 89996215, compound

Product 1

HCID 89996213HCID 89996213, compoundYield 231%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
130 °C

Procedure

Trimethylsilylazide (1.2 mL, 9.21 mmol) was added to a solution of 6-ethynyl-2-methoxy-3-nitropyridine (Preparation 200, 0.082 g, 0.460 mmol) in toluene (10.2 mL). The reaction mixture was stirred at 130° C. for 48 hours. The reaction was diluted with water and concentrated in vacuo. The residue was purified using Biotage silica gel column chromatography eluting with cyclohexane/EtOAc 70/30 to 50/50 to afford the title compound as a beige solid (235 mg, 77%).

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was purified
  3. washeluting with cyclohexane/EtOAc 70/30 to 50/50

Sources & evidence

ORD record
ord-ee7812dabddc4ffca58796bafa5195a3
Source dataset
uspto-grants-2016_08
Patent number
US09409907B2

Reaction notes

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