Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 3-(Methylsulfonyl)phenylboronic acid | HCID 2773542 | — |
| Reactant | HCID 136081961 | HCID 136081961 | — |
| Catalyst | Cupric acetate | HCID 8895 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 59631781 | HCID 59631781 | 35.7% |
Reaction Steps
A mixture of 4-(1-(2-chlorophenyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl)phenol (169 mg, 0.5 mmol), 3-methylsulfonylphenylboronic acid (200 mg, 1 mmol), Cu(OAc)2 (181 mg, 1 mmol), and NEt3 (35 μL, 2.5 mmol) and molecule sieves (4A) in DCM was shaken overnight at 20° C. Solid was removed by filtration and filtrate was evaporated to give a crude, which was purified by column chromatography on silica gel eluting with EtOAc-hexane (1:4 to 1:2) to afford 1-(2-chlorophenyl)-5-(4-{[3-(methylsulfonyl)phenyl]oxy}phenyl)-3-(trifluoromethyl)-1H-pyrazole (88 mg). 1H-NMR: CDCl3: 7.68 (m, 1H), 7.55 (m, 2H), 7.48 (m, 1H), 7.62-7.40 (m, 2H), 7.27 (m, 2H), 7.21 (m, 1H), 6.93 (m, 1H), 6.80 (s, 1H), 3.04 (s, 3H), MS(ES): 493 [M+H]+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08703805B2 |
|---|
| Source dataset | uspto-grants-2014_04 |
|---|
| ORD ID | ord-d20308cf800f44d1be54b66b7e965101 |
|---|
| Source note | uspto-grants-2014_04 |
|---|