Azido(trimethyl)stannane → HCID 178450054, compound

HRID 480462Notes

Reaction equation

HRID 480462 reaction equation
[OH:1][C:2]([C:30]1[CH:31]=[C:32]2[C:37](=[CH:38][CH:39]=1)[CH:36]=[C:35]([C:40]#[N:41])[CH:34]=[CH:33]2)([C:6]1[N:7]=[CH:8][N:9](C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[CH:10]=1)[CH:3]([CH3:5])[CH3:4].[N:42]([Sn](C)(C)C)=[N+:43]=[N-:44]>C1(C)C=CC=CC=1>[NH:9]1[CH:10]=[C:6]([C:2]([C:30]2[CH:39]=[CH:38][C:37]3[C:32](=[CH:33][CH:34]=[C:35]([C:40]4[NH:41][N:44]=[N:43][N:42]=4)[CH:36]=3)[CH:31]=2)([OH:1])[CH:3]([CH3:5])[CH3:4])[N:7]=[CH:8]1

Participants

4

Reactant 2

HCID 5104973Azido(trimethyl)stannaneHCID 18769121HCID 18769121, compound

Product 1

HCID 178450054HCID 178450054, compoundYield 74.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 6-(1-hydroxy-2-methyl-1-(1-trityl-1H-imidazol-4-yl)propyl)-2-naphthonitrile (1.0 g) and azidotrimethyltin (770 mg) in toluene (10 mL) was refluxed for 48 h. The precipitate was collected by filtration, dissolved in THF-methanol (1:1) and concentrated. The residue was diluted with water and extracted with a mixed solution of ethyl acetate-THF (1:1). The extract was dried and concentrated. The residue was purified by column chromatography (eluent; hexane:THF=1:3) and crystallized from ethyl acetate to give the titled compound (469 mg) as a pale yellow powder.

Workup

  1. filtrationThe precipitate was collected by filtration
  2. dissolutiondissolved in THF-methanol (1:1)
  3. concentrationconcentrated
  4. additionThe residue was diluted with water
  5. extractionextracted with a mixed solution of ethyl acetate-THF (1:1)
  6. customThe extract was dried
  7. concentrationconcentrated
  8. customThe residue was purified by column chromatography (eluent; hexane:THF=1:3)
  9. customcrystallized from ethyl acetate

Sources & evidence

ORD record
ord-36f70bbc89474d2e84f1e5788c5cf704
Source dataset
uspto-grants-2003_11
Patent number
US06649643B1

Reaction notes

Loading…