HuagongsheHuagongshe Chemistry Print Report · For research reference only
Ethyl Acetate → 5-(2-Ethyl-5-methylsulfonylphenyl)-1-methylpyridin-2-one
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Ethyl Acetate | HCID 8857 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | 1-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2(1H)-one | HCID 45480194 | — |
| Reactant | 1-Ethyl-2-iodo-4-(methylsulfonyl)benzene | HCID 58521830 | — |
| Catalyst | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| Solvent | 1,4-Dioxane--water (1/1) | HCID 21886435 | — |
| Product | 5-(2-Ethyl-5-methylsulfonylphenyl)-1-methylpyridin-2-one | HCID 118021599 | 97.1% |
Reaction Steps
The title compound of step 3 (62 mg, 0.2 mmol), 1-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-one (57 mg, 0.24 mmol), K2CO3 (82 mg, 0.6 mmol), Pd(dppf)Cl2 (6.2 mg) in 1,4-dioxane/water (4:1) (5 mL) were heated at 85° C. under N2 overnight. Silica gel chromatography (PE:EA=1:1) gave the title compound (56.6 mg, 97%) as a brown oil. 1H NMR (300 MHz, CDCl3): δ 1.66 (3H, t, J=6.0 Hz), 2.63-2.71 (2H, m), 3.05 (3H, s), 3.60 (3H, s), 6.64 (1H, d, J=9.0 Hz), 7.28-7.33 (2H, m), 7.48 (1H, d, J=9.0 Hz), 7.70 (1H, s), 7.82-7.85 (1H, m). LCMS: 292 (M+1)+
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09115114B2 |
| Source dataset | uspto-grants-2015_08 |
| ORD ID | ord-8a6a8404c8e748d58a2c1c0216941602 |
| Source note | uspto-grants-2015_08 |