Dibutyltin oxide → HCID 178420158, compound

HRID 1668660Notes

Reaction equation

HRID 1668660 reaction equation
[NH:1]1[C:9]2[C:4](=[C:5]([CH2:10][NH:11][C:12]3[N:17]=[C:16]([C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=4)[N:15]=[C:14]([C:24]4[CH:25]=[N:26][CH:27]=[C:28]([CH:31]=4)[C:29]#[N:30])[CH:13]=3)[CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.C[Si]([N:36]=[N+:37]=[N-:38])(C)C.C([Sn](=O)CCCC)CCC>COCCOC>[NH:1]1[C:9]2[C:4](=[C:5]([CH2:10][NH:11][C:12]3[CH:13]=[C:14]([C:24]4[CH:25]=[N:26][CH:27]=[C:28]([C:29]5[NH:38][N:37]=[N:36][N:30]=5)[CH:31]=4)[N:15]=[C:16]([C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=4)[N:17]=3)[CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1

Participants

5

Reactant 3

HCID 61221Dibutyltin oxideHCID 78378AzidotrimethylsilaneHCID 67329788HCID 67329788, compound

Product 1

HCID 178420158HCID 178420158, compound

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

A solution of 5-(6-[(1H-indol-4-ylmethyl)-amino]-2-pyridin-2-yl-pyrimidin-4-yl)-nicotinonitrile (Ex. 2.9) (50 mg, 0.124 mmol) in DME (2 ml) under an inert atmosphere of argon is treated with trimethylsilyl azide (5 eq, 70 mg, 0.248) and dibutyltin oxide (0.3 eq, 9.3 mg). The resulting mixture is heated at reflux for 4 hours and then allowed to cool to room temperature. On cooling, a solid precipitates which is collected by filtration, washed with MeOH and dried in vacuo at 40° C. overnight to afford the title compound [M+H]+=447.

Workup

  1. temperatureThe resulting mixture is heated
  2. temperatureat reflux for 4 hours
  3. temperatureOn cooling
  4. customa solid precipitates which
  5. filtrationis collected by filtration
  6. washwashed with MeOH
  7. customdried in vacuo at 40° C. overnight

Sources & evidence

ORD record
ord-3466cf0a2d85443485750ee05287a5d8
Source dataset
uspto-grants-2011_08
Patent number
US07989458B2

Reaction notes

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