Azido(trimethyl)stannane → HCID 178439913, compound

HRID 2255573Notes

Reaction equation

HRID 2255573 reaction equation
[C:1]([CH:3]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][N:12]2[C:16]3=[N:17][CH:18]=[CH:19][C:20]([CH3:21])=[C:15]3[N:14]=[C:13]2[CH2:22][CH2:23][CH3:24])=[CH:7][CH:6]=1)#[N:2].C[Sn]([N:35]=[N+:36]=[N-:37])(C)C>C1(C)C=CC=CC=1>[CH3:21][C:20]1[CH:19]=[CH:18][N:17]=[C:16]2[N:12]([CH2:11][C:8]3[CH:7]=[CH:6][C:5]([CH2:4][CH:3]([C:25]4[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=4)[C:1]4[NH:37][N:36]=[N:35][N:2]=4)=[CH:10][CH:9]=3)[C:13]([CH2:22][CH2:23][CH3:24])=[N:14][C:15]=12

Participants

4

Reactant 2

HCID 5104973Azido(trimethyl)stannaneHCID 197381193-[4-(2-cyano-2-phenylethyl)phenyl]methyl-7-methyl-2-propyl-3H-imidazo[4,5-b]pyridine

Product 1

HCID 178439913HCID 178439913, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of the product of the product of Step E (46 mg, 0.12 mmol) in toluene (2 mL) was added 29 mg (0.14 mmol) of trimethylstannyl azide and the reaction mixture was refluxed for 24 hours. The reaction mixture was concentrated in vacuo. The residue was dissolved in THF and treated with 12N HCl (5 drops) for 5 minutes at room temperature. The mixture was concentrated in vacuo and purified on a silica gel flash chromatography column eluted with CHCl3 /MeOH/NH4OH (80:20:2) to afford 19.6 mg (38%) of the title compound.

Workup

  1. temperaturethe reaction mixture was refluxed for 24 hours
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. dissolutionThe residue was dissolved in THF
  4. additiontreated with 12N HCl (5 drops) for 5 minutes at room temperature
  5. concentrationThe mixture was concentrated in vacuo
  6. custompurified on a silica gel flash chromatography column
  7. washeluted with CHCl3 /MeOH/NH4OH (80:20:2)

Sources & evidence

ORD record
ord-031a2e7fb03840ec953c0d49a9df9cbb
Source dataset
uspto-grants-1993_08
Patent number
US05240938

Reaction notes

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