Trimethylsilylmethyl Azide → HCID 59525895, compound

HRID 386067

Reaction equation

HRID 386067 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH:8]([F:11])[C:9]#[CH:10])[N:3]=1.[CH3:12][Si:13]([CH2:16][N:17]=[N+:18]=[N-:19])([CH3:15])[CH3:14].O=C1O[C@H]([C@H](CO)O)C([O-])=C1O.[Na+]>CC(O)(C)C.O.C([O-])(O)=O.[Na+]>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH:8]([F:11])[C:9]2[N:19]=[N:18][N:17]([CH2:16][Si:13]([CH3:15])([CH3:14])[CH3:12])[CH:10]=2)[N:3]=1

Participants

7

Reactant 3

HCID 150751Trimethylsilylmethyl AzideHCID 23667548Sodium AscorbateHCID 595259492-Bromo-6-(1-fluoroprop-2-yn-1-yl)pyridine

Product 1

HCID 59525895HCID 59525895, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolvent3×HCID 6386tert-ButanolSolventHCID 516892Sodium BicarbonateSolvent

Procedure

2-Bromo-6-(1-fluoroprop-2-yn-1-yl)pyridine (520 mg, 2.43 mmol) and trimethylsilylmethyl azide (377 mg, 2.92 mmol) were combined in t-BuOH (5.0 mL) and water (3.0 mL). CuSO4.5H2O (30 mg, 0.12 mmol) in water (1.0 mL) was added, followed by sodium ascorbate (96 mg, 0.49 mmol) in water (1.0 mL). The reaction was stirred at room temperature overnight, diluted with saturated NaHCO3, and extracted with EtOAc (2×). The combined organic layers were washed with brine, dried (MgSO4), filtered, and evaporated to a brown residue that was purified by flash chromatography (0-30% EtOAc/hexanes) to afford the title compound as a colorless solid.

Workup

  1. extractionextracted with EtOAc (2×)
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customevaporated to a brown residue that
  6. customwas purified by flash chromatography (0-30% EtOAc/hexanes)

Sources & evidence

ORD record
ord-91ced9ba13bd4ff0b33a986cbd7427cc
Source dataset
uspto-grants-2013_02
Patent number
US08367706B2

Linked notes

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