Azidotrimethylsilane → HCID 58994998, compound

HRID 536946Notes

Reaction equation

HRID 536946 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:14]#[N:15])[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)=[CH:4][C:3]=1[Br:16].C[Si]([N:21]=[N+:22]=[N-:23])(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>CCOC(C)=O>[Br:16][C:3]1[CH:4]=[C:5]([C:8]2([C:14]3[N:21]=[N:22][NH:23][N:15]=3)[CH2:9][CH2:10][O:11][CH2:12][CH2:13]2)[CH:6]=[CH:7][C:2]=1[NH2:1]

Participants

5

Reactant 3

HCID 78378AzidotrimethylsilaneHCID 2724141Tetrabutylammonium FluorideHCID 68832685HCID 68832685, compound

Product 1

HCID 58994998HCID 58994998, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 4-(4-amino-3-bromo-phenyl)-tetrahydro-pyran-4-carbonitrile (as prepared in the previous step, 141 mg, 0.500 mmol), trimethylsilylazide (133 μL, 1.00 mmol) and tetrabutylammonium fluoride (65 mg, 0.25 mmol) was stirred at 120° C. for 18 h under Ar. After cooling to RT, the mixture was treated with 30 mL of EtOAc and washed with H2O (2×10 mL), 15% citric acid aqueous solution (3×10 mL) and brine (10 mL). After drying over Na2SO4, the organic layer was concentrated in vacuo to afford the title compound (147 mg, 91%) as a faint yellow solid. Mass spectrum (ESI, m/z): Calcd. for C12H14BrN5O, 324.0 (M+H). found 324.1.

Workup

  1. temperatureAfter cooling to RT
  2. washwashed with H2O (2×10 mL), 15% citric acid aqueous solution (3×10 mL) and brine (10 mL)
  3. dry with materialAfter drying over Na2SO4
  4. concentrationthe organic layer was concentrated in vacuo

Sources & evidence

ORD record
ord-58030c228d5342709c0ed8d07ea44849
Source dataset
uspto-grants-2014_10
Patent number
US08859602B2

Reaction notes

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