Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | 3-Tolylboronic acid | HCID 2733950 | — |
| Reactant | HCID 58546913 | HCID 58546913 | — |
| Catalyst | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | HCID 58547347 | HCID 58547347 | 87.3% |
Reaction Steps
To a stirred solution of 3-(3-bromo-pyridin-2-yl)-azetidine-1-carboxylic acid tert-butyl ester (3) (150 mg, 0.48 mmol) in dioxane (10 mL) was added phenylboronic acid (78) (87 mg, 0.71 mmol), Na2CO3 (152 mg, 1.4 mmol) and H2O (2 mL). The reaction mixture was degassed with N2 and then PdCl2(dppf) (35 mg, 0.05 mmol) was added. The reaction mixture was stirred at 80° C. for 12 h. The reaction mixture was left to reach RT and filtered through a pad of CELITE® and the filter cake was washed with CH2Cl2 (20 mL×3). The combined filtrates were evaporated in vacuo and the residue was purified by column chromatography ((EtOAc:Petrol ether=3:1) to give the desired compound (79) (130 mg, 87% yield). ESI-MS (M+1): 311 calc. for C19H22N2O2 310.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08957073B2 |
|---|
| Source dataset | uspto-grants-2015_02 |
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| ORD ID | ord-829bce7c28494257b79a41f5b5a19406 |
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| Source note | uspto-grants-2015_02 |
|---|
