HuagongsheHuagongshe Chemistry Print Report · For research reference only
Potassium Carbonate → 4-{2-[(3R)-3-(Fluoromethyl)pyrrolidin-1-yl]ethyl}-5-methyl-2-[4'-(methylsulfonyl)biphenyl-4-yl]-1,3-oxazole
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | Triphenylphosphine | HCID 11776 | — |
| Reactant | 4-(Methanesulfonyl)phenylboronic acid | HCID 2734364 | — |
| Reactant | 2-(4-Bromophenyl)-4-{2-[(3R)-3-(fluoromethyl)pyrrolidin-1-yl]ethyl}-5-methyl-1,3-oxazole | HCID 11632032 | — |
| Catalyst | palladium(II) acetate | HCID 167845 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Product | 4-{2-[(3R)-3-(Fluoromethyl)pyrrolidin-1-yl]ethyl}-5-methyl-2-[4'-(methylsulfonyl)biphenyl-4-yl]-1,3-oxazole | HCID 11690789 | 36.6% |
Reaction Steps
Prepare using the method of Example 103 with palladium (II) acetate (0.003 g, 0.01 mmol), anhydrous acetonitrile (4 mL), triphenylphosphine (0.014 g, 0.05 mmol), distilled water (1 mL), 4-(methanesulfonyl)benzeneboronic acid (0.15 g, 0.71 mmol), 2-(4-bromophenyl)-4-{2-[(3R)-3-(fluoromethyl)pyrrolidin-1-yl]ethyl}-5-methyl-1,3-oxazole (See Example 112) (0.25 g, 0.68 mmol) and potassium carbonate (0.28 g, 2.04 mmol). Additionally triturate the resulting solid with 2:1 diethyl ether:ethyl acetate to give the title compound as a pale yellow coloured solid (0.11 g): MS (m/e): 443 (M+1).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07666871B2 |
| Source dataset | uspto-grants-2010_02 |
| ORD ID | ord-c72353d9d1d54f83b772567f6aeebb24 |
| Source note | uspto-grants-2010_02 |