1-Heptyne → 5-hept-1-ynyl-1-methyl-3-phenyl-1H-pyrazole

HRID 1967193Notes

Reaction equation

HRID 1967193 reaction equation
[CH3:1][N:2]1[C:6](OS(C2C=CC(C)=CC=2)(=O)=O)=[CH:5][C:4]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[N:3]1.[CH:24]#[C:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30]>CCCCCCC.C(Cl)Cl>[C:24]([C:6]1[N:2]([CH3:1])[N:3]=[C:4]([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH:5]=1)#[C:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30]

Participants

4

Reactant 2

HCID 123501-HeptyneHCID 866466171-methyl-3-phenyl-1H-pyrazol-5-yl 4-methylbenzene-1-sulfonate

Product 1

HCID 252219465-hept-1-ynyl-1-methyl-3-phenyl-1H-pyrazole

Reagents, catalysts & solvents 1

HCID 21907733Dichloromethane heptaneSolvent

Procedure

This product was prepared from toluene-4-sulfonic acid 2-methyl-5-phenyl-2H-pyrazol-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 (120 mg, 95%); 1H NMR δ (CDCl3): 7.78 (d, J=8.20 Hz, 2H), 7.42-7.33 (t, J=8.05 Hz, 2H), 7.32 (m, 1H), 6.62 (s, 1H), 3.93 (s, 3H), 2.48 (t, J=7.25 Hz, 2H), 1.65 (p, J=7.18 Hz, 2H), 1.5-1.32 (m, 4H), 0.94 (t, J=7.22 Hz, 3H); LCMS m/z: 252.

Workup

  1. customfor the Sonogashira cross-coupling reaction
  2. customyield (120 mg, 95%)

Sources & evidence

ORD record
ord-b928166627174a389b1ddb4ffac8a1bb
Source dataset
uspto-grants-2013_04
Patent number
US08420812B2

Reaction notes

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