Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | 3,6-Dihydro-2H-pyran-4-boronic acid pinacol ester | HCID 11218053 | — |
| 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 | Water | HCID 962 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | HCID 58547379 | HCID 58547379 | 80% |
Reaction Steps
To a solution of 3-(3-chloro-pyrazin-2-yl)-azetidine-1-carboxylic acid tert-butyl ester (7) (1.0 g, 3.7 mmol) in dioxane (16 mL) was added a solution of Na2CO3 (780 mg, 6.4 mmol) in 5 mL water, followed by additional of 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-3,6-dihydro-2H-pyran (114) (purchased from WUXI APPTEC) (840 mg 4.0 mmol) and Pd(dppf)Cl2 (80 mg). The resulting mixture was heated to reflux overnight under N2 atmosphere. TLC showed that the staring material was consumed completely. The solution was filtered and the filtrate was concentrated to give the residue which was purified by ISCO silica gel column (10% to 80% EtOAc in petroleum ether) to give the product 3-[3-(3,6-dihydro-2H-pyran-4-yl)-pyrazin-2-yl]-azetidine-1-carboxylic acid tert-butyl ester (115) (938 mg, 2.96 mmol, yield 80%) as solid. ESI-MS (M+1): 318 calc. for C17H23N3O3 317.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08957073B2 |
|---|
| Source dataset | uspto-grants-2015_02 |
|---|
| ORD ID | ord-a3ef1ff9a61e41789d675652bfac15e7 |
|---|
| Source note | uspto-grants-2015_02 |
|---|
