Dibutyltin oxide → HCID 56839771, compound

HRID 1466885Notes

Reaction equation

HRID 1466885 reaction equation
[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([Cl:17])[CH:15]=2)[C:10]([O:18][C:19]2[CH:20]=[C:21]([CH2:25][C:26]#[N:27])[CH:22]=[CH:23][CH:24]=2)=[C:9]1[CH3:28])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N:29]([Si](C)(C)C)=[N+:30]=[N-:31].C([Sn](=O)CCCC)CCC>C1(C)C=CC=CC=1>[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([Cl:17])[CH:15]=2)[C:10]([O:18][C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([CH2:25][C:26]3[N:29]=[N:30][NH:31][N:27]=3)[CH:20]=2)=[C:9]1[CH3:28])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 61221Dibutyltin oxideHCID 78378AzidotrimethylsilaneHCID 56839770HCID 56839770, compound

Product 1

HCID 56839771HCID 56839771, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
90 °C

Procedure

[3-(1-Benzyl-6-chloro-2-methyl-1H-indol-3-yloxy)-phenyl]-acetonitrile (0.030 g, 0.078 mmol) was dissolved in toluene (1 mL) along with azidotrimethylsilane (44 μL, 0.33 mmol) and dibutyltin(IV) oxide (0.002 g, 0.008 mmol). The reaction was heated to 90° C. for 2 days then concentrated. The crude material was dissolved in DMSO and purified via preparatory HPLC to give the title compound.

Workup

  1. concentrationthen concentrated
  2. dissolutionThe crude material was dissolved in DMSO
  3. custompurified via preparatory HPLC

Sources & evidence

ORD record
ord-b9e55bda0f69461c8751ff0e49a680c9
Source dataset
uspto-grants-2015_04
Patent number
US09000025B2

Reaction notes

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