Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Tetrahydrofuran | HCID 8028 | — |
| Reactant | Potassium Phosphate, Tribasic | HCID 62657 | — |
| Reactant | (6-Chloropyridin-3-yl)methanol | HCID 177161 | — |
| Reactant | 1-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole | HCID 2773987 | — |
| Catalyst | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 60209896 | HCID 60209896 | — |
Reaction Steps
To a pressure vessel was charged Pd(dppf)Cl2 (CH2Cl2 adduct, 341 mg, 0.418 mmol) and potassium phosphate (1.48 g, 6.97 mmol). Nitrogen was blown over the solids and THF (8 mL) and H2O (1.6 mL) were added. A solution of 2-chloro-5-hydroxymethylpyridine (500 mg, 3.48 mmol) and 1-methylpyrazole-4-boronic acid pinacol ester (797 mg, 3.83 mmol) was added; the resulting solution was capped and heated at 80° C. overnight, then cooled to rt and diluted with ethyl acetate. The organic solution was washed 1× with saturated aqueous sodium bicarbonate and 1× with brine, dried over sodium sulfate, filtered, and concentrated in vacuo. The residue was purified via silica gel chromatography, eluting with 30-100% ethyl acetate in hexanes to provide [6-(1-methyl-1H-pyrazol-4-yl)pyridin-3-yl]methanol that gave a mass ion (ES+) of 190.1 for [M+H]+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08557992B2 |
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| Source dataset | uspto-grants-2013_10 |
|---|
| ORD ID | ord-556e321bb714400cb5b46a3612a41639 |
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| Source note | uspto-grants-2013_10 |
|---|
