HuagongsheHuagongshe Chemistry Print Report · For research reference only
Methanol → 1-Benzyl-2-methyl-5-(2,4-difluorophenyl)-1H-imidazole
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Methanol | HCID 887 | — |
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | 2,4-Difluorophenylboronic acid | HCID 2734334 | — |
| Reactant | 1-Benzyl-2-methyl-5-bromo-1H-imidazole | HCID 66868795 | — |
| Catalyst | Palladium(2+) acetate--triphenylphosphane (1/2/2) | HCID 84538 | — |
| Solvent | 1,2-Dimethoxyethane | HCID 8071 | — |
| Product | 1-Benzyl-2-methyl-5-(2,4-difluorophenyl)-1H-imidazole | HCID 66869085 | 67.5% |
Reaction Steps
Heat a mixture of 1-benzyl-2-methyl-5-bromo-1H-imidazole (4.71 g, 18.7 mmol), 2,4-difluorophenyl boronic acid (6.92 g, 43.8 mmol), bis(acetato)bis(triphenylphosphine)-palladium(II) (1.4 g, 1.875 mmol), 2N Na2CO3 (19 mL, 38 mmol), MeOH (19 mL) and 1,2-dimethoxyethane (120 mL) to reflux for 18 h. Cool to RT. Add water and EtOAc and separate the layers. Dry organic layer over MgSO4, filter, and concentrate. Purify the residue (silica gel chromatography, eluting with EtOAc:CH2Cl2 mixtures) to give the desired compound (3.59 g).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07582652B2 |
| Source dataset | uspto-grants-2009_09 |
| ORD ID | ord-663562bcc74b4a6da309af86daf84192 |
| Source note | uspto-grants-2009_09 |