Azidotrimethylsilane → HCID 178450726, compound

HRID 2359986Notes

Reaction equation

HRID 2359986 reaction equation
[C:1]([O:5][C:6](=[O:28])[C:7]1[CH:12]=[CH:11][C:10]([N:13]2[C:17]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[CH:16][CH:15]=[C:14]2[CH2:24][CH2:25][C:26]#[N:27])=[CH:9][CH:8]=1)([CH3:4])([CH3:3])[CH3:2].[N:29]([Si](C)(C)C)=[N+:30]=[N-:31]>C1(C)C=CC=CC=1>[C:1]([O:5][C:6](=[O:28])[C:7]1[CH:12]=[CH:11][C:10]([N:13]2[C:14]([CH2:24][CH2:25][C:26]3[NH:31][N:30]=[N:29][N:27]=3)=[CH:15][CH:16]=[C:17]2[C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)=[CH:9][CH:8]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 78378AzidotrimethylsilaneHCID 67223534HCID 67223534, compound

Product 1

HCID 178450726HCID 178450726, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

To a stirred solution of 4-[2-(2-cyano-ethyl)-5-phenyl-pyrrol-1yl]-benzoic acid tert-butyl ester (2.31 mmol, 1.0 eq.) in toluene (12 ml) were added Azidotrimethylsilane (TMSN3) (4.62 mmol, 2.0 eq.) and Sn(Bu)2O (dibutyltin(IV) oxide) (0.23 mmol, 0.1 eq.). The resulting mixture was heated to 110° C. overnight. The solvent was evaporated in vacuo and the residue loaded onto a 40 g RediSep silica-gel column for purification. Gradient elution with methanol/DCM (0% to 7% methanol in DCM over 25 minutes) gave the product 4-{2-phenyl-5-[2-(1H-tetrazol-5-yl)ethyl]-pyrrol-1-yl}-benzoic acid tert-butyl ester as a light yellow oil after combination of the appropriate fractions and evaporation of the solvent in vacuo, 62% yield.

Workup

  1. customThe solvent was evaporated in vacuo
  2. customthe residue loaded onto a 40 g RediSep silica-gel column for purification
  3. washGradient elution with methanol/DCM (0% to 7% methanol in DCM over 25 minutes)

Sources & evidence

ORD record
ord-726034b4bb784a21bf8eac8347594efd
Source dataset
uspto-grants-2014_04
Patent number
US08686015B2

Reaction notes

Loading…