5-Phenyl-1-pentyne → HCID 25222066, compound

HRID 1967203Notes

Reaction equation

HRID 1967203 reaction equation
[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10](OS(C2C=CC(C)=CC=2)(=O)=O)=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:28]([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[CH2:29][CH2:30][C:31]#[CH:32]>CCCCCCC.C(Cl)Cl>[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([C:32]#[C:31][CH2:30][CH2:29][CH2:28][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)=[N:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 745735-Phenyl-1-pentyneHCID 86646619HCID 86646619, compound

Product 1

HCID 25222066HCID 25222066, compound

Reagents, catalysts & solvents 1

HCID 21907733Dichloromethane heptaneSolvent

Procedure

This product was prepared from toluene-4-sulfonic acid 1-benzyl-1H-indazol-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 (87.5 mg, 50%); δH (CDCl3): 7.92 (d, J=8.11 Hz, 1H), 7.4-7.19 (m, 8H), 7.15-7.08 (m, 5H), 5.5 (s, 2H), 2.76 (t, J=7.16 Hz, 2H), 2.4 (t, J=7.15 Hz, 2H), 1.91 (p, J=7.21 Hz, 2H); LCMS m/z: 350.

Workup

  1. customfor the Sonogashira cross-coupling reaction
  2. customyield (87.5 mg, 50%)

Sources & evidence

ORD record
ord-53d3e55610614ab886c3f5632f253267
Source dataset
uspto-grants-2013_04
Patent number
US08420812B2

Reaction notes

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