1-Heptyne → HCID 68498012, compound

HRID 1967205Notes

Reaction equation

HRID 1967205 reaction equation
[C:1]1([CH3:27])[CH:6]=[CH:5][C:4]([N:7]2[C:11]3=[N:12][CH:13]=[CH:14][CH:15]=[C:10]3[C:9](OS(C3C=CC(C)=CC=3)(=O)=O)=[N:8]2)=[CH:3][CH:2]=1.[CH:28]#[C:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34]>CCCCCCC>[C:28]([C:5]1[CH:6]=[C:1]([CH3:27])[CH:2]=[CH:3][C:4]=1[N:7]1[C:11]2=[N:12][CH:13]=[CH:14][CH:15]=[C:10]2[CH:9]=[N:8]1)#[C:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34]

Participants

4

Reactant 2

HCID 123501-HeptyneHCID 86646620HCID 86646620, compound

Product 1

HCID 68498012HCID 68498012, compound

Reagents, catalysts & solvents 1

HCID 8900HeptaneSolvent

Procedure

This product was prepared from toluene-4-sulfonic acid 1-p-tolyl-1H-pyrazolo[3,4-b]pyridin-3-yl ester and 1-heptyne following the general procedure for the Sonogashira cross-coupling reaction described above. Chromatography eluent: heptane/iPr2ether 1:1; yield (110 mg, 73%); 1H NMR δ (CDCl3): 8.63 (m, 1H), 8.19 (m, 1H), 8.10 (d, J=8.55 Hz, 2H), 7.32 (d, J=8.46 Hz, 2H), 7.20-7.27 (m, 1H), 2.53 (t, J=7.23 Hz, 2H), 2.39 (s, 3H), 1.71 (p, J=7.19 Hz, 2H), 1.57-1.46 (m, 2H), 1.45-1.33 (m, 2H), 0.94 (t, J=7.20 Hz, 3H); LCMS m/z: 303.

Workup

  1. customfor the Sonogashira cross-coupling reaction
  2. customyield (110 mg, 73%)

Sources & evidence

ORD record
ord-933a9a512c29483eb52caed41526b913
Source dataset
uspto-grants-2013_04
Patent number
US08420812B2

Reaction notes

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