5-Phenyl-1-pentyne → 1-Methyl-3phenyl-5-(5-phenyl-pent-1-ynyl)-1H-pyrazole

HRID 1967192Notes

Reaction equation

HRID 1967192 reaction equation
[CH3:1][N:2]1[C:6](OS(C2C=CC(C)=CC=2)(=O)=O)=[CH:5][C:4]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[N:3]1.[CH2:24]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[CH2:25][CH2:26][C:27]#[CH:28]>CCCCCCC.C(Cl)Cl>[CH3:1][N:2]1[C:6]([C:28]#[C:27][CH2:26][CH2:25][CH2:24][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[CH:5][C:4]([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)=[N:3]1

Participants

4

Reactant 2

HCID 745735-Phenyl-1-pentyneHCID 866466171-methyl-3-phenyl-1H-pyrazol-5-yl 4-methylbenzene-1-sulfonate

Product 1

HCID 252219451-Methyl-3phenyl-5-(5-phenyl-pent-1-ynyl)-1H-pyrazole

Reagents, catalysts & solvents 1

HCID 21907733Dichloromethane heptaneSolvent

Procedure

This product was prepared from toluene-4-sulfonic acid 2-methyl-5-phenyl-2H-pyrazol-3-yl ester and pent-4-ynyl-benzene following the general procedure for the Sonogashira cross-coupling reaction described above. Chromatography eluent: heptane/DCM 1:1; yield (80 mg, 53%); 1H NMR δ (CDCl3): 7.78 (d, J=8.21 Hz, 2H), 7.43-7.22 (m, 8H), 6.62 (s, 1H), 3.98 (s, 3H), 2.78 (t, J=7.30 Hz, 2H), 2.43 (t, J=7.19 Hz, 2H), 1.96 (p, J=7.33 Hz, 2H); LCMS m/z: 300.

Workup

  1. customfor the Sonogashira cross-coupling reaction
  2. customyield (80 mg, 53%)

Sources & evidence

ORD record
ord-7299410050054271b383a504069dcd0e
Source dataset
uspto-grants-2013_04
Patent number
US08420812B2

Reaction notes

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