Azidotrimethylsilane → HCID 178457652, compound

HRID 1851888Notes

Reaction equation

HRID 1851888 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[CH:14]=[CH:13][C:12]([CH2:15][N:16]2[C:24]3[C:19](=[CH:20][C:21]([C:25]([NH:27][CH:28]([C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=4)[CH2:29][CH3:30])=[O:26])=[CH:22][CH:23]=3)[C:18]([CH3:37])=[C:17]2[CH3:38])=[CH:11][CH:10]=1)#[N:2].[Si]([N:43]=[N+:44]=[N-:45])(C)(C)C>C1(C)C=CC=CC=1>[NH:43]1[C:1]([C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=2[C:9]2[CH:10]=[CH:11][C:12]([CH2:15][N:16]3[C:24]4[C:19](=[CH:20][C:21]([C:25]([NH:27][CH:28]([C:31]5[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=5)[CH2:29][CH3:30])=[O:26])=[CH:22][CH:23]=4)[C:18]([CH3:37])=[C:17]3[CH3:38])=[CH:13][CH:14]=2)=[N:2][N:45]=[N:44]1

Participants

4

Reactant 2

HCID 78378AzidotrimethylsilaneHCID 49852647HCID 49852647, compound

Product 1

HCID 178457652HCID 178457652, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 1-((2′-cyano-[1,1′-biphenyl]-4-yl)methyl)-2,3-dimethyl-N-(1-phenylpropyl)-1H-indole-5-carboxamide (27 mg, 0.05 mmol, 1 equiv) in toluene (0.6 mL) in a high-pressure vial were added TMSN3 (14 μL, 0.05 mmol, 2 equiv) and Bu2SnO (2 mg, 0.005 mmol, 0.1 equiv). The vial was sealed and the reaction mixture was heated at reflux for 2 h. After concentration, the residue was purified by preparative HPLC to afford a beige powder. ESI-MS (m/z): 541 [M+H]+.

Workup

  1. customThe vial was sealed
  2. temperaturethe reaction mixture was heated
  3. temperatureat reflux for 2 h
  4. concentrationAfter concentration
  5. customthe residue was purified by preparative HPLC
  6. customto afford a beige powder

Sources & evidence

ORD record
ord-61fd430a104a498d9d127e0023a2ea6d
Source dataset
uspto-grants-2015_02
Patent number
US08957093B2

Reaction notes

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