Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | 2-(Methoxycarbonyl)-4-pyridineboronic acid, pinacol ester | HCID 17750517 | — |
| Reactant | 4-Bromo-6-(trifluoromethyl)-1H-indazole | HCID 24729232 | — |
| Catalyst | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | Trifluoroacetic acid | HCID 6422 | — |
| Product | 4-(6-(trifluoromethyl)-1H-indazol-4-yl)picolinic acid | HCID 89782841 | — |
Reaction Steps
A mixture of 4-bromo-6-(trifluoromethyl)-1H-indazole (0.302 g, 1.140 mmol), methyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)picolinate (0.3 g, 1.140 mmol), and PdCl2(dppf) (0.042 g, 0.057 mmol) in dioxane (10 mL) was combined with aqueous saturated NaHCO3 (3 mL) to give a light brown suspension. The reaction mixture was heated in a microwave reactor at 140° C. for 45 minutes and was then cooled, filtered, concentrated in vacuo, and purified by preparative HPLC (Waters SunFire C18, 5 μm, 30 mm ID×75 mm column) eluting with a gradient of 15-55% ACN (containing 0.035% TFA) in water (containing 0.05% TFA) to give a TFA salt of the title compound. ESI-MS m/z [M+H]+ calc'd for C14H8F3N3O2, 308.1. found 308.1.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US09434743B2 |
|---|
| Source dataset | uspto-grants-2016_09 |
|---|
| ORD ID | ord-8b092a4b92984b9087448cbb51eecf8c |
|---|
| Source note | uspto-grants-2016_09 |
|---|
