Dibutyltin oxide → HCID 178506099, compound

HRID 735478Notes

Reaction equation

HRID 735478 reaction equation
[CH2:1]([N:8]1[C:16]([C:17]2[CH:18]=[C:19]([CH:30]=[CH:31][CH:32]=2)[O:20][CH2:21][C:22]2[CH:29]=[CH:28][C:25]([C:26]#[N:27])=[CH:24][CH:23]=2)=[C:15]2[C:10]([C:11]([C:33]([F:36])([F:35])[F:34])=[CH:12][CH:13]=[CH:14]2)=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[Si]([N:41]=[N+:42]=[N-:43])(C)C.C([Sn](=O)CCCC)CCC>C1(C)C=CC=CC=1>[CH2:1]([N:8]1[C:16]([C:17]2[CH:32]=[CH:31][CH:30]=[C:19]([O:20][CH2:21][C:22]3[CH:29]=[CH:28][C:25]([C:26]4[NH:43][N:42]=[N:41][N:27]=4)=[CH:24][CH:23]=3)[CH:18]=2)=[C:15]2[C:10]([C:11]([C:33]([F:36])([F:34])[F:35])=[CH:12][CH:13]=[CH:14]2)=[N:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 61221Dibutyltin oxideHCID 78378AzidotrimethylsilaneHCID 67021380HCID 67021380, compound

Product 1

HCID 178506099HCID 178506099, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

4-({3-[2-Benzyl-7-(trifluoromethyl)-2H-indazol-3-yl]phenoxy}methyl)benzonitrile (37 mg, 1 eq) was treated with trimethylsilyl azide (21 μL, 2 eq) and di-n-butyltin oxide (5 mg, 0.3 eq) in toluene (2.5 mL) at 100° C. until full conversion. After cooling, most of the solvent was removed in vacuo and the residue was taken in methanol. Purification by flash chromatography, eluent 10% methanol in dichloromethane, afforded the title compound in 87% yleld.

Workup

  1. temperatureAfter cooling, most of the solvent
  2. customwas removed in vacuo
  3. customPurification by flash chromatography, eluent 10% methanol in dichloromethane

Sources & evidence

ORD record
ord-f2aa312446e3494ca070dd830c168cd5
Source dataset
uspto-grants-2009_09
Patent number
US07592363B2

Reaction notes

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