1-Ethynylcyclohexene → 5-cyclohex-1-enylethynyl-1methyl-3-phenyl-1H-pyrazole

HRID 1967194Notes

Reaction equation

HRID 1967194 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.[C:24]([C:26]1[CH2:31][CH2:30][CH2:29][CH2:28][CH:27]=1)#[CH:25]>CCCCCCC.C(Cl)Cl>[C:26]1([C:24]#[C:25][C:6]2[N:2]([CH3:1])[N:3]=[C:4]([C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)[CH:5]=2)[CH2:31][CH2:30][CH2:29][CH2:28][CH:27]=1

Participants

4

Reactant 2

HCID 791281-EthynylcyclohexeneHCID 866466171-methyl-3-phenyl-1H-pyrazol-5-yl 4-methylbenzene-1-sulfonate

Product 1

HCID 252219475-cyclohex-1-enylethynyl-1methyl-3-phenyl-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 1-ethynyl-cyclohexene following the general procedure for the Sonogashira cross-coupling reaction described above. Chromatography eluent: heptane/DCM 1:1; yield (110 mg, 84%); 1H NMR δ (CDCl3): 7.78 (d, J=8.09 Hz, 2H), 7.42-7.33 (t, J=8.11 Hz, 2H), 7.32 (m, 1H), 6.62 (s, 1H), 6.31-6.27 (m, 1H), 3.94 (s, 3H), 2.14-2.22 (m, 4H), 1.58-1.73 (m, 4H); LCMS m/z: 246.

Workup

  1. customfor the Sonogashira cross-coupling reaction
  2. customyield (110 mg, 84%)

Sources & evidence

ORD record
ord-931308dad3e04c77963401d9bafdcf6c
Source dataset
uspto-grants-2013_04
Patent number
US08420812B2

Reaction notes

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