Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Potassium Phosphate, Tribasic | HCID 62657 | — |
| Reactant | 3-Tolylboronic acid | HCID 2733950 | — |
| Reactant | Tert-butyl 3-(3-chloropyrazin-2-yl)azetidine-1-carboxylate | HCID 59351411 | — |
| Catalyst | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | HCID 58547022 | HCID 58547022 | 92% |
Reaction Steps
To a solution of 3-(3-chloro-pyrazin-2-yl)-azetidine-1-carboxylic acid tert-butyl ester (7) (540 mg, 2.0 mmol, Preparation 2), 3-methyl-phenylboronic acid (78) (299.2 mg, 2.2 mmol), K3PO4 (818 mg, 4.0 mmol), in dioxane (20 mL) and water (4 mL) was added Pd(dppf)Cl2 (73.2 mg, 0.1 mmol) then the reaction mixture was stirred at 90° C. under nitrogen atmosphere overnight. The reaction mixture was filtered through CELITE® and washed with EtOAc (50 mL). The filtrate was concentrated and the crude product was purified by silica gel column to give 3-(3-m-tolyl-pyrazin-2-yl)-azetidine-1-carboxylic acid tert-butyl ester (30) (597 mg, 1.84 mmol, yield 91.85%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08957073B2 |
|---|
| Source dataset | uspto-grants-2015_02 |
|---|
| ORD ID | ord-d2c933342c224dbca597af4cf406bd2f |
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| Source note | uspto-grants-2015_02 |
|---|
