HCID 14972071, compound → HCID 70034970, compound

HRID 1370177Notes

Reaction equation

HRID 1370177 reaction equation
[CH3:1][N:2]1[C:6](=[O:7])[N:5]([CH:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]2=[CH:14][O:15][C:16]2[CH:21]=[CH:20][C:19](I)=[CH:18][C:17]=2[CH3:23])[N:4]=[N:3]1.[C:24]1([N:30]2[CH:34]=[C:33]([Sn](CCCC)(CCCC)CCCC)[CH:32]=[N:31]2)[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:1][N:2]1[C:6](=[O:7])[N:5]([CH:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]2=[CH:14][O:15][C:16]2[CH:21]=[CH:20][C:19]([C:33]3[CH:32]=[N:31][N:30]([C:24]4[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=4)[CH:34]=3)=[CH:18][C:17]=2[CH3:23])[N:4]=[N:3]1

Participants

5

Reactant 2

HCID 14972071HCID 14972071, compoundHCID 70035422HCID 70035422, compound

Product 1

HCID 70034970HCID 70034970, compoundYield 15.7%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Procedure

A solution of 1.48 g (3.5 mmol) of the tetrazolone from Example 5, 1.51 g of (1-phenylpyrazol-4-yl)tributylstannane and 0.2 g of tetrakis(triphenylphosphine)palladium(0) in 20 ml of anhydrous toluene was stirred at 70° C. for 2 hours and then refluxed for 2 hours. The solvent was distilled off and the residue was chromatographed over silica gel (cyclohexane:methyl tert-butyl ether mixture 1:1), giving 0.24 g of the title compound of m.p. 152-153° C.

Workup

  1. temperaturerefluxed for 2 hours
  2. distillationThe solvent was distilled off
  3. customthe residue was chromatographed over silica gel (cyclohexane:methyl tert-butyl ether mixture 1:1)

Sources & evidence

ORD record
ord-7e91b44c95034146bcdc793584ecd0f2
Source dataset
uspto-grants-2003_06
Patent number
US06583090B1

Reaction notes

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