Azidotrimethylsilane → HCID 178419355, compound

HRID 385747

Reaction equation

HRID 385747 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]#[CH:9])=[CH:4][CH:3]=1.C[Si]([N:14]=[N+:15]=[N-:16])(C)C.O=C1O[C@H]([C@H](CO)O)C([O-])=C1O.[Na+]>CC(O)(C)C.O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:14]=[N:15][NH:16][CH:9]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 78378AzidotrimethylsilaneHCID 136603Benzene, 1-bromo-4-ethynyl-HCID 23667548Sodium Ascorbate

Product 1

HCID 178419355HCID 178419355, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent4×HCID 6386tert-ButanolSolvent

Conditions

Temperature
100 °C

Procedure

1-Bromo-4-ethynylbenzene (650 mg, 3.59 mmol) and trimethylsilyl azide (3.57 mL, 26.9 mmol) were combined in t-BuOH (5.0 mL) and water (3.0 mL) CuSO4.5H2O (90 mg, 0.36 mmol) in water (1.0 mL) and sodium ascorbate (285 mg, 1.44 mmol) in water (1.0 mL) were added, and the sealed reaction mixture was stirred at 100° C. for 48 h. The mixture was diluted with water and extracted with EtOAc (3×). The combined organic layers were washed with brine, dried (MgSO4), filtered, and evaporated. Flash chromatography (dry load, 0-50% EtOAc/hexanes) afforded the title compound as a colorless solid.

Workup

  1. customthe sealed reaction mixture
  2. extractionextracted with EtOAc (3×)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customevaporated
  7. dry with materialFlash chromatography (dry load, 0-50% EtOAc/hexanes)

Sources & evidence

ORD record
ord-e1d2c4c42db4498d8be0729f57f379c5
Source dataset
uspto-grants-2013_02
Patent number
US08367706B2

Linked notes

Loading…