Azido(trimethyl)stannane → HCID 178441773, compound

HRID 1742406Notes

Reaction equation

HRID 1742406 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:7]=[C:8]([CH2:29][CH2:30][CH2:31][CH3:32])[N:9]([CH:12]2[C:20]3[C:15](=[CH:16][C:17]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=4[C:27]#[N:28])=[CH:18][CH:19]=3)[CH2:14][CH2:13]2)[C:10]=1[Cl:11])=[O:5])[CH3:2].C[Sn]([N:37]=[N+:38]=[N-:39])(C)C>C1(C)C=CC=CC=1>[CH2:1]([O:3][C:4]([C:6]1[N:7]=[C:8]([CH2:29][CH2:30][CH2:31][CH3:32])[N:9]([CH:12]2[C:20]3[C:15](=[CH:16][C:17]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=4[C:27]4[NH:39][N:38]=[N:37][N:28]=4)=[CH:18][CH:19]=3)[CH2:14][CH2:13]2)[C:10]=1[Cl:11])=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 5104973Azido(trimethyl)stannaneHCID 15228953HCID 15228953, compound

Product 1

HCID 178441773HCID 178441773, compoundYield 24.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 2-butyl-5-chloro-1-[5-(2-cyano-phenyl)-indan-1-yl]-1H-imidazole-4-carboxylic acid ethyl ester (177 mg, 0.41 mmol) and trimethyltin azide (108 mg, 0.5 mmol) was heated in toluene (1.0 mL)for 72 hours. The reaction mixture was cooled to room temperature and concentrated in vacuo. The residue was chromatographed on SiO2 -gel using a gradient of 2% MeOH/CH2Cl2 to 15% MeOH/CH2Cl2 to give 50 mg of a colorless oil.

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was chromatographed on SiO2

Sources & evidence

ORD record
ord-289c0c7ac16d419b93c13b2467ae6d80
Source dataset
uspto-grants-1994_08
Patent number
US05338740

Reaction notes

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