Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | 5-Bromo-2-methanesulfonylpyridine | HCID 13433424 | — |
| Reactant | 3-Cyclohexyl-2-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-prop-2-en-1-ol | HCID 67084599 | — |
| Catalyst | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 67484356 | HCID 67484356 | 59.2% |
Reaction Steps
Add 5-bromo-2-methanesulfonyl-pyridine (0.47 g, 2.0 mmol), [1,1′-bis(diphenylphosphino)ferrocene]-dichloropalladium(II) (163 mg, 0.2 mmol), and Na2CO3 (2.5 mL, 2.0 M, 5.0 mmol) to a solution of 3-cyclohexyl-2-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-prop-2-en-1-ol (0.53 g, 2.2 mmol) in DMF (10 mL). Stir at 80° C. for 18 h, monitor completion of the reaction by LCMS. Treat the reaction mixture with water and extract 3 times with MTBE. Dry organic layers over sodium sulfate and remove solvents under vacuum to obtain 0.72 g crude product. Purification by silica gel chromatography, eluting with gradient from 10:0 to 8:2 dichloromethane:MTBE affords 350 mg (E)-3-cyclohexyl-2-(6-methanesulfonyl-pyridin-3-yl)-prop-2-en-1-ol. MS (m/e): 296 (M+H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US07576108B2 |
|---|
| Source dataset | uspto-grants-2009_08 |
|---|
| ORD ID | ord-7955e4bffd9f4a9ca44f89b82a1bb47f |
|---|
| Source note | uspto-grants-2009_08 |
|---|
