Toluene → HCID 178441893, compound

HRID 2082055Notes

Reaction equation

HRID 2082055 reaction equation
[CH2:1]([C:5]1[N:6]([CH2:20][C:21]2[CH:26]=[CH:25][C:24]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=3[C:33]#[N:34])=[CH:23][CH:22]=2)[C:7]2[N:8]([C:10]([CH3:19])=[C:11]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[N:12]=2)[N:9]=1)[CH2:2][CH2:3][CH3:4].C[Sn]([N:39]=[N+:40]=[N-:41])(C)C.C1(C)C=CC=CC=1>C(Cl)Cl>[CH2:1]([C:5]1[N:6]([CH2:20][C:21]2[CH:22]=[CH:23][C:24]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=3[C:33]3[NH:41][N:40]=[N:39][N:34]=3)=[CH:25][CH:26]=2)[C:7]2[N:8]([C:10]([CH3:19])=[C:11]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[N:12]=2)[N:9]=1)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 1140TolueneHCID 5104973Azido(trimethyl)stannaneHCID 10003659HCID 10003659, compound

Product 1

HCID 178441893HCID 178441893, compoundYield 38.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A mixture of 95.0 mg (0.213 mmol) of 2-butyl-3-[(2'-cyanobiphenyl-4-yl)methyl]-6-methyl-5-phenyl-3H-imidazo[1,2-b][1,2,4]triazole (from Step F), 158 mg (0.769 mmol) of trimethyltin azide, and 2.0 ml of toluene was stirred at reflux under N2 for 24 hours. The mixture was concentrated in vacuo, and the residue was treated with 3 ml of dry MeOH and 1.0 g of silica gel. The resulting mixture was stirred at room temperature in a stoppered flask overnight. The solvent was removed by rotary evaporation in vacuo to give a dry powder, which was added as a slurry in CH2Cl2 to the top of a column of silica gel (26×2.5 cm) packed in CH2Cl2. Gradient elution of the column with 1.5% MeOH in CH2Cl2 and concentration of the product fractions yielded 40.4 mg (37%) of the title compound as a yellow gum, which, upon trituration with ether, was transformed to a tan solid (28 mg, 25%), mp 207°-208° C.; homogeneous by TLC in 90:10:0.1 CH2Cl2 -MeOH-AcOH.

Workup

  1. temperatureat reflux under N2 for 24 hours
  2. concentrationThe mixture was concentrated in vacuo
  3. additionthe residue was treated with 3 ml of dry MeOH and 1.0 g of silica gel
  4. stirringThe resulting mixture was stirred at room temperature in a stoppered flask overnight
  5. customThe solvent was removed by rotary evaporation in vacuo
  6. customto give a dry powder, which
  7. washGradient elution of the column with 1.5% MeOH in CH2Cl2 and concentration of the product fractions

Sources & evidence

ORD record
ord-03579c0956224896afab549ba7e706db
Source dataset
uspto-grants-1993_02
Patent number
US05187179

Reaction notes

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