1-Heptyne → HCID 25222065, compound

HRID 1967202Notes

Reaction equation

HRID 1967202 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.[CH:28]#[C:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34]>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:28]#[C:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])=[N:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 123501-HeptyneHCID 86646619HCID 86646619, compound

Product 1

HCID 25222065HCID 25222065, 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-heptyne following the general procedure for the Sonogashira cross-coupling reaction described above. Chromatography eluent: heptane/DCM 1:1; yield (84 mg, 54%); 1H NMR δ (CDCl3): 7.9 (d, J=8.02 Hz, 1H), 7.4-7.19 (m, 8H), 5.5 (s, 2H), 2.48 (t, J=7.22 Hz, 2H), 1.65 (p, J=7.18 Hz, 2H), 1.5-1.32 (m, 4H), 0.94 (t, J=7.21 Hz, 3H); LCMS m/z: 302.

Workup

  1. customfor the Sonogashira cross-coupling reaction
  2. customyield (84 mg, 54%)

Sources & evidence

ORD record
ord-c44c7cac72d7495a9d04b6727cab846c
Source dataset
uspto-grants-2013_04
Patent number
US08420812B2

Reaction notes

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