5-Phenyl-1-pentyne → HCID 25221835, compound

HRID 1967188Notes

Reaction equation

HRID 1967188 reaction equation
[CH3:1][N:2]1[C:6]([C:7]([F:10])([F:9])[F:8])=[CH:5][C:4](OS(C2C=CC(C)=CC=2)(=O)=O)=[N:3]1.[CH2:22]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[CH2:23][CH2:24][C:25]#[CH:26]>CCCCCCC.C(Cl)Cl>[CH3:1][N:2]1[C:6]([C:7]([F:8])([F:9])[F:10])=[CH:5][C:4]([C:26]#[C:25][CH2:24][CH2:23][CH2:22][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[N:3]1

Participants

4

Reactant 2

HCID 745735-Phenyl-1-pentyneHCID 44543018HCID 44543018, compound

Product 1

HCID 25221835HCID 25221835, compound

Reagents, catalysts & solvents 1

HCID 21907733Dichloromethane heptaneSolvent

Procedure

This product was prepared from toluene-4-sulfonic acid 1-methyl-5-trifluoromethyl-1H-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 7:3; yield (86 mg, 60%); 1H NMR δ (CDCl3): 7.31-7.25 (m, 2H), 7.22-7.16 (m, 3H), 6.64 (s, 1H), 3.98 (s, 3H), 2.78 (t, J=7.44 Hz, 2H), 2.42 (t, J=7.04 Hz, 2H), 1.95 (p, J=7.33 Hz, 2H); LCMS m/z: 292.

Workup

  1. customfor the Sonogashira cross-coupling reaction
  2. customyield (86 mg, 60%)

Sources & evidence

ORD record
ord-e783feb3ce58435682b0b814a0587411
Source dataset
uspto-grants-2013_04
Patent number
US08420812B2

Reaction notes

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