HuagongsheHuagongshe Chemistry Print Report · For research reference only
2-Bromo-1-(cyclopropylmethoxy)-4-(methylsulfonyl)benzene → US10023592, Example 119
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 2-Bromo-1-(cyclopropylmethoxy)-4-(methylsulfonyl)benzene | HCID 118021693 | — |
| Reactant | 3-Fluoro-1-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-one | HCID 123823790 | — |
| Catalyst | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| Solvent | Bicarbonate Ion | HCID 769 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | US10023592, Example 119 | HCID 118022321 | 46% |
Reaction Steps
3-Fluoro-1-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-one (40 mg, 0.16 mmol), 2-bromo-1-(cyclopropylmethoxy)-4-methanesulfonylbenzene (49 mg, 0.16 mmol), and Pd(dppf)Cl2 (12 mg, 10%) in 1,4-dioxane (880 μL) and saturated bicarbonate solution (aq) (220 μL) were reacted, worked up, and purified in a manner similar to Example 117. The title compound (22 mg, 46%) was obtained as a tan solid. 1H NMR (400 MHz, DMSO-d6) δ 0.31-0.42 (m, 2H) 0.53-0.63 (m, 2H) 1.17-1.34 (m, 1H) 3.20 (s, 3H) 3.58 (s, 3H) 3.95-4.06 (m, 2H) 7.24-7.33 (m, 1H) 7.72-7.79 (m, 1H) 7.80-7.87 (m, 1H) 7.84 (s, 1H) 7.88-7.93 (m, 1H) LCMS (M+H)+=351.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09034900B2 |
| Source dataset | uspto-grants-2015_05 |
| ORD ID | ord-a8b6cb4ef04a4499a6acdcbd05fdacea |
| Source note | uspto-grants-2015_05 |