Azido(trimethyl)stannane → HCID 178439913, compound

HRID 2399464Notes

Reaction equation

HRID 2399464 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-15b72564fd5945a197a5fd49f29f6275
Source dataset
uspto-grants-1995_09
Patent number
US05449682

Reaction notes

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