HuagongsheHuagongshe Chemistry Print Report · For research reference only
Cesium carbonate → 4-(1-Acetyl-2,3-dihydro-1H-indol-6-ylamino)-N-cyclopropylmethyl-2-trifluoromethyl-benzenesulfonamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | 1-Acetyl-6-aminoindoline | HCID 258564 | — |
| Reactant | Binap, (A+-)- | HCID 634876 | — |
| Reactant | 4-bromo-N-(cyclopropylmethyl)-2-(trifluoromethyl)benzenesulfonamide | HCID 24948367 | — |
| Catalyst | palladium(II) acetate | HCID 167845 | — |
| Solvent | Toluene | HCID 1140 | — |
| Product | 4-(1-Acetyl-2,3-dihydro-1H-indol-6-ylamino)-N-cyclopropylmethyl-2-trifluoromethyl-benzenesulfonamide | HCID 24946884 | — |
Reaction Steps
A mixture of 4-Bromo-N-cyclopropylmethyl-2-trifluoromethyl-benzenesulfonamide (51 mg), Pd(OAc)2 (3.2 mg), BINAP (14 mg), cesium carbonate (55 mg) and 1-(6-Amino-2,3-dihydro-indol-1-yl)-ethanone (50 mg) in 15 ml toluene was relaxed for 12 hours. The reaction mixture was eluted through a silica bed with Toluene and then with PE:EtOAc (70:30). The toluene fraction was discarded and the solvent of the PE:EtOAc fraction was removed under reduced pressure. The crude product was purified by Combiflash (linear gradient PE-THF). Yield 32 mg, 49%.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09422235B2 |
| Source dataset | uspto-grants-2016_08 |
| ORD ID | ord-8f51e8c669a848b9b331306e20f012b0 |
| Source note | uspto-grants-2016_08 |