Azidotrimethylsilane → HCID 178450726, compound

HRID 1261409Notes

Reaction equation

HRID 1261409 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-5a03712d6a764a33a5d59754d69b331d
Source dataset
uspto-grants-2013_06
Patent number
US08470857B2

Reaction notes

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