Azido(trimethyl)stannane → HCID 178441472, compound

HRID 274571Notes

Reaction equation

HRID 274571 reaction equation
[CH2:1]([C:5]1[N:9]([CH2:10][C:11]2[CH:16]=[CH:15][C:14]([C:17]3[C:18]4[CH:27]=[CH:26][CH:25]=[CH:24][C:19]=4[O:20][C:21]=3[C:22]#[N:23])=[CH:13][CH:12]=2)[C:8]2[C:28]([C:32]([O:34][CH3:35])=[O:33])=[CH:29][CH:30]=[CH:31][C:7]=2[N:6]=1)[CH2:2][CH2:3][CH3:4].C[Sn]([N:40]=[N+:41]=[N-:42])(C)C>C1(C)C=CC=CC=1>[CH2:1]([C:5]1[N:9]([CH2:10][C:11]2[CH:16]=[CH:15][C:14]([C:17]3[C:18]4[CH:27]=[CH:26][CH:25]=[CH:24][C:19]=4[O:20][C:21]=3[C:22]3[NH:42][N:41]=[N:40][N:23]=3)=[CH:13][CH:12]=2)[C:8]2[C:28]([C:32]([O:34][CH3:35])=[O:33])=[CH:29][CH:30]=[CH:31][C:7]=2[N:6]=1)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 5104973Azido(trimethyl)stannaneHCID 20093026HCID 20093026, compound

Product 1

HCID 178441472HCID 178441472, compoundYield 91.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of methyl 2-butyl-1-[[4-(2-cyanobenzo[b]furan-3-yl)phenyl]methyl]benzimidazole-7-carboxylate (1.3 g) and trimethyltin azide (2.9 g) in toluene (125 ml) was heated under reflux for 2 days. After concentration to dryness, the residue was dissolved in a mixture of methanol (150 ml) and 1N hydrochloric acid (25 ml) and the mixture was stirred at room temperature for 3 hours. The reaction mixture was concentrated to dryness and the residue was dissolved in methylene chloride. The resulting solution was washed with water, dried and concentrated to dryness. The residue was purified by column chromatography on silica gel to give pale yellow powders (1.3 g).

Workup

  1. temperatureunder reflux for 2 days
  2. concentrationAfter concentration to dryness
  3. dissolutionthe residue was dissolved in a mixture of methanol (150 ml) and 1N hydrochloric acid (25 ml)
  4. concentrationThe reaction mixture was concentrated to dryness
  5. dissolutionthe residue was dissolved in methylene chloride
  6. washThe resulting solution was washed with water
  7. customdried
  8. concentrationconcentrated to dryness
  9. customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-efce413f9ec44a34a948e93979190164
Source dataset
uspto-grants-1995_02
Patent number
US05389641

Reaction notes

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