Azido(trimethyl)stannane → HCID 178437433, compound

HRID 1492618Notes

Reaction equation

HRID 1492618 reaction equation
[C:1]([CH:3]([N:10]([C:12]1[CH:17]=[CH:16][C:15]([CH2:18][N:19]2[C:23]3=[N:24][C:25]([CH3:29])=[CH:26][C:27]([CH3:28])=[C:22]3[N:21]=[C:20]2[CH2:30][CH3:31])=[CH:14][CH:13]=1)[CH3:11])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)#[N:2].C[Sn]([N:36]=[N+:37]=[N-:38])(C)C>C1(C)C=CC=CC=1>[NH:36]1[C:1]([CH:3]([N:10]([C:12]2[CH:13]=[CH:14][C:15]([CH2:18][N:19]3[C:23]4=[N:24][C:25]([CH3:29])=[CH:26][C:27]([CH3:28])=[C:22]4[N:21]=[C:20]3[CH2:30][CH3:31])=[CH:16][CH:17]=2)[CH3:11])[C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=2)=[N:2][N:38]=[N:37]1

Participants

4

Reactant 2

HCID 5104973Azido(trimethyl)stannaneHCID 10319349HCID 10319349, compound

Product 1

HCID 178437433HCID 178437433, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 101 mg (0.25 mmol) of the product of Step A dissolved in 5.0 mL toluene was added 154 mg (0.75 mmol) of trimethylstannyl azide, and the mixture was stirred and heated at reflux for 24 hours. The reaction mixture was evaporated in vacuo, the residue was redissolved in 5.0 mL THF and then treated with 0.5 mL of a 1.0N HCl solution at 0° C. After stirring for 10 minutes, the reaction mixture was concentrated in vacuo, and the water was removed by azeotropic distillation with toluene. After evaporation, the residue was purified on a silica gel preparative layer chromatography plate eluted with CHCl3 /MeOH/NH4OH (80:20:2). The product bands were collected and the product removed from the silica gel by elution with 10% methanol/chloroform. Evaporation of the filtrate and recrystallization of the residue from dichloromethane/hexanes afforded 90 mg (80%) of the title compound as a white powder.

Workup

  1. temperatureheated
  2. temperatureat reflux for 24 hours
  3. customThe reaction mixture was evaporated in vacuo
  4. dissolutionthe residue was redissolved in 5.0 mL THF
  5. additiontreated with 0.5 mL of a 1.0N HCl solution at 0° C
  6. stirringAfter stirring for 10 minutes
  7. concentrationthe reaction mixture was concentrated in vacuo
  8. customthe water was removed by azeotropic distillation with toluene
  9. customAfter evaporation
  10. customthe residue was purified on a silica gel preparative layer chromatography plate
  11. washeluted with CHCl3 /MeOH/NH4OH (80:20:2)
  12. customThe product bands were collected
  13. customthe product removed from the silica gel by elution with 10% methanol/chloroform
  14. customEvaporation of the filtrate and recrystallization of the residue from dichloromethane/hexanes

Sources & evidence

ORD record
ord-5c7bc09d80574ff78ef65cedb93179a8
Source dataset
uspto-grants-1994_12
Patent number
US05374638

Reaction notes

Loading…