Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | 4-(Trifluoromethyl)phenylboronic acid | HCID 2734389 | — |
| Reactant | Ethyl 1-(6-{2-[(4-bromophenyl)(difluoro)methoxy]phenyl}pyridin-2-yl)-5-(trifluoromethyl)-1H-pyrazole-4-carboxylate | HCID 86633499 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Product | Trifluoroacetic acid | HCID 6422 | — |
| Product | 1-[6-(2-{Difluoro[4'-(trifluoromethyl)biphenyl-4-yl]methoxy}phenyl)pyridin-2-yl]-5-(trifluoromethyl)-1H-pyrazole-4-carboxylic acid | HCID 25231362 | — |
Reaction Steps
A mixture of the title compound from Example 300 Step A (50.0 mg, 0.086 mmol), 4-trifluoromethylphenylboronic acid (35 mg, 0.18 mmol), trans-dichlorobis(triphenylphosphine) palladium (II) (9.0 mg, 0.013 mmol), Na2CO3 (0.1 mL, 2.0 M aqueous, 0.2 mmol), and MeCN (1 mL) was stirred at 90° C. for 35 min. The crude mixture was dried concentrated in vacuo. Treatment with a mixture of 0.1 mL each of 3 N NaOH, dioxane and MeOH at 50° C. for 10 min, followed by reverse phase HPLC using a YMC C-18 column (65 to 100% acetonitrile in water, each with 0.1% v/v TFA) provided the title compound: LCMS m/z 599.9 [M−F]+; 1H NMR (500 MHz, acetone-d6) δ 8.34 (m, 2H), 8.03 (d, J=7.6 Hz, 1H), 7.99 (d, J=8.2 Hz, 1H), 7.95-7.78 (m, 7H), 7.69 (d, J=8.5 Hz, 2H), 7.62 (m, 2H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08455638B2 |
|---|
| Source dataset | uspto-grants-2013_06 |
|---|
| ORD ID | ord-2516cbb24b7847b9b300ffa6c5a9b6f2 |
|---|
| Source note | uspto-grants-2013_06 |
|---|
