3,5-Dimethylpyrazole → HCID 69748164, compound

HRID 1061856Notes

Reaction equation

HRID 1061856 reaction equation
[CH3:1][O:2][C:3](=[O:20])[C:4]1[CH:9]=[CH:8][C:7]([CH:10](Cl)[C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([O:17][CH3:18])[CH:12]=2)=[CH:6][CH:5]=1.[CH3:21][C:22]1[CH:26]=[C:25]([CH3:27])[NH:24][N:23]=1>CC#N.[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH3:1][O:2][C:3](=[O:20])[C:4]1[CH:9]=[CH:8][C:7]([CH:10]([N:23]2[C:22]([CH3:21])=[CH:26][C:25]([CH3:27])=[N:24]2)[C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([O:17][CH3:18])[CH:12]=2)=[CH:6][CH:5]=1

Participants

5

Reactant 2

HCID 62103,5-DimethylpyrazoleHCID 69747323HCID 69747323, compound

Product 1

HCID 69748164HCID 69748164, compoundYield 30%

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 6342AcetonitrileSolvent

Procedure

To a stirring solution of 4-[Chloro-(3-methoxy-phenyl)-methyl]-benzoic acid methyl ester (5.0 g, 17.3 mmol) in 87 mL CH3CN was added 3,5-dimethyl pyrazole (5.0 g, 51.8 mmol) and tetra-n-butyl ammonium iodide (3.2 g, 8.6 mmol). The mixture was heated to reflux for 24 h, cooled to room temperature and concentrated under reduce pressure. The crude oil was purified by flash chromatography with 30% ethyl acetate/hexanes, collecting 8 mL fractions. The product containing fractions were collected and concentrated under reduce pressure to give the desired product (1.8 g, 30%) as a clear yellow oil. 400 MHz 1H NMR (CDCl3) δ 7.97 (d, J=8.5 Hz, 2H), 7.19-7.25 (m, 3H), 6.81-6.83 (m, 1H), 6.68-6.73 (m, 2H), 6.52 (s, 1H), 5.85 (s, 1H), 3.89 (s, 3H), 3.72 (s, 3H), 2.20 (s, 3H), 2.16 (s, 3H); MS (M+1) 351.2.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 24 h
  3. concentrationconcentrated
  4. customThe crude oil was purified by flash chromatography with 30% ethyl acetate/hexanes
  5. customcollecting 8 mL fractions
  6. additionThe product containing fractions
  7. customwere collected
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-2324b8a40d804ef8bcd958e21172f0ef
Source dataset
uspto-grants-2005_11
Patent number
US06960609B2

Reaction notes

Loading…