HuagongsheHuagongshe Chemistry Print Report · For research reference only
Cesium carbonate → 6-Chloro-2-(3-oxo-cyclopent-1-enyl)-quinoline-5-carboxylic acid (4,4-difluoro-1-hydroxy-cyclohexyl methyl)-amide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | 3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-2-cyclopenten-1-one | HCID 66822876 | — |
| Reactant | 2,6-Dichloro-quinoline-5-carboxylic acid (4,4-difluoro-1-hydroxy-cyclohexylmethyl)-amide | HCID 118556092 | — |
| Product | 6-Chloro-2-(3-oxo-cyclopent-1-enyl)-quinoline-5-carboxylic acid (4,4-difluoro-1-hydroxy-cyclohexyl methyl)-amide | HCID 118566706 | — |
Reaction Steps
The title compound was synthesized according to the procedure described in example 125 using 2,6-dichloro-quinoline-5-carboxylic acid (4,4-difluoro-1-hydroxy-cyclo hexyl methyl)-amide, cesium carbonate, 3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-cyclopent-2-enone and tetrakis(triphenyl phosphine)palladium(0). 1H NMR (400 MHz, DMSO-d6) δ ppm 8.83-8.86 (bs, 1H), 8.27-8.29 (m, 1H), 8.22 (d, J=8.8 Hz, 1H), 8.12-8.14 (m, 1H), 7.87 (d, J=9.1 Hz, 1H), 7.12 (s, 1H), 4.72 (s, 1H), 3.42-3.44 (m, 2H), 3.20-3.22 (m, 2H), 2.55-2.57 (m, 2H), 2.07-2.10 (m, 2H), 1.89-2.01 (m, 2H), 1.70-1.77 (m, 4H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09399623B2 |
| Source dataset | uspto-grants-2016_07 |
| ORD ID | ord-cb3e447e4d634e7f893f4a8e5cee2aa4 |
| Source note | uspto-grants-2016_07 |