Furfuryl Alcohol → 5-(5-(4-Chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazol-3-yl)-1-(furan-2-ylmethyl)-1H-tetrazole

HRID 254827Notes

Reaction equation

HRID 254827 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([C:13]3[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][C:14]=3[Cl:20])[N:11]=[C:10]([C:21]3[NH:25][N:24]=[N:23][N:22]=3)[C:9]=2[CH3:26])=[CH:4][CH:3]=1.[CH2:27](O)[C:28]1[O:32][CH:31]=[CH:30][CH:29]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([C:13]3[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][C:14]=3[Cl:20])[N:11]=[C:10]([C:21]3[N:25]([CH2:27][C:28]4[O:32][CH:31]=[CH:30][CH:29]=4)[N:24]=[N:23][N:22]=3)[C:9]=2[CH3:26])=[CH:4][CH:3]=1

Participants

5

Reactant 4

HCID 7361Furfuryl AlcoholHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 178422378HCID 178422378, compound

Product 1

HCID 248100905-(5-(4-Chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazol-3-yl)-1-(furan-2-ylmethyl)-1H-tetrazoleYield 16.2%

Conditions

Temperature
0 °C

Procedure

A mixture of 5-(5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazol-3-yl)-1H-tetrazole (113 mg, 0.28 mmol) obtained in Step 1 of Example 52, furfuryl alcohol (0.05 ml, 0.56 mmol) and triphenylphosphine (146 mg, 0.56 mmol) was dissolved in tetrahydronfuran (3 ml) and cooled down to 0° C. Then, diisopropyl azodicarboxylate (0.11 ml, 0.56 mmol) was slowly added thereto at 0° C. After stirring for 2 hours at room temperature, the resulting solution was quenched with saturated ammonium chloride solution (1 ml). The mixture was extracted with ethyl acetate, and then the solvent of the organic layer was removed under a reduced pressure. The residue contained two regioisomers were separated by silica gel column chromatography (hexane/ethyl acetate=1/5), and repurified by reverse phase preparative HPLC, to obtain two compound, one of which was the title compound (22 mg, 16%).

Workup

  1. dissolutionwas dissolved in tetrahydronfuran (3 ml)
  2. customat 0° C
  3. customthe resulting solution was quenched with saturated ammonium chloride solution (1 ml)
  4. extractionThe mixture was extracted with ethyl acetate
  5. customthe solvent of the organic layer was removed under a reduced pressure
  6. customwere separated by silica gel column chromatography (hexane/ethyl acetate=1/5)
  7. customrepurified by reverse phase preparative HPLC
  8. customto obtain two compound, one of which

Sources & evidence

ORD record
ord-88f6f0f67b3e48368a6c80765d83b94f
Source dataset
uspto-grants-2011_01
Patent number
US07875647B2

Reaction notes

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