1-Ethynylcyclohexene → HCID 25222064, compound

HRID 1967201Notes

Reaction equation

HRID 1967201 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.[C:28]([C:30]1[CH2:35][CH2:34][CH2:33][CH2:32][CH:31]=1)#[CH:29]>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:29]#[C:28][C:30]2[CH2:35][CH2:34][CH2:33][CH2:32][CH:31]=2)=[N:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 791281-EthynylcyclohexeneHCID 86646619HCID 86646619, compound

Product 1

HCID 25222064HCID 25222064, 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 1-ethynyl-cyclohexene following the general procedure for the Sonogashira cross-coupling reaction described above. Chromatography eluent: heptane/DCM 1:1; yield (81.5, 54%); 1H NMR δ (CDCl3): 7.8 (d, J=8.05 Hz, 1H), 7.4-7.19 (m, 8H), 6.37-6.3 (m, 1H), 5.6 (s, 2H), 2.14-2.22 (m, 4H), 1.58-1.73 (m, 4H); LCMS m/z: 312.

Workup

  1. customfor the Sonogashira cross-coupling reaction
  2. customyield (81.5, 54%)

Sources & evidence

ORD record
ord-b9158b2d565d4dc78286c339cf39e25d
Source dataset
uspto-grants-2013_04
Patent number
US08420812B2

Reaction notes

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