3-Ethynylthiophene → 1-Methyl-3-phenyl-5-thiophen-3-ylethynyl-1H-pyrazole

HRID 1967196Notes

Reaction equation

HRID 1967196 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[CH:30]=[CH:29][S:28][CH:27]=1)#[CH:25]>CCCCCCC.CCOC(C)=O>[CH3:1][N:2]1[C:6]([C:25]#[C:24][C:26]2[CH:30]=[CH:29][S:28][CH:27]=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 35484223-EthynylthiopheneHCID 866466171-methyl-3-phenyl-1H-pyrazol-5-yl 4-methylbenzene-1-sulfonate

Product 1

HCID 252219491-Methyl-3-phenyl-5-thiophen-3-ylethynyl-1H-pyrazole

Reagents, catalysts & solvents 1

HCID 21899848Ethylacetate heptaneSolvent

Procedure

This product was prepared from toluene-4-sulfonic acid 2-methyl-5-phenyl-2H-pyrazol-3-yl ester and 3-ethynyl-thiophene following the general procedure for the Sonogashira cross-coupling reaction described above. Chromatography eluent: heptane/EtOAc 95:5; yield (60 mg, 45%); 1H NMR δ (CDCl3): 7.78 (d, J=8.10 Hz, 2H), 7.60 (m, 1H), 7.46-7.29 (m, 4H), 7.22 (m, 1H), 6.77 (s, 1H), 4.05 (s, 3H); LCMS m/z: 264.

Workup

  1. customfor the Sonogashira cross-coupling reaction
  2. customyield (60 mg, 45%)

Sources & evidence

ORD record
ord-653c92c2772b4cd18d23e50f26611ac8
Source dataset
uspto-grants-2013_04
Patent number
US08420812B2

Reaction notes

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