HuagongsheHuagongshe Chemistry Print Report · For research reference only
Ammonia → HCID 66804021, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Ammonia | HCID 222 | — |
| Reactant | 8-Hydroxyquinoline | HCID 1923 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | 3-Bromo-4-(trifluoromethyl)pyridine | HCID 19937263 | — |
| Reactant | HCID 68094318 | HCID 68094318 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Solvent | Dimethyl Sulfoxide | HCID 679 | — |
| Solvent | Water | HCID 962 | — |
| Product | HCID 66804021 | HCID 66804021 | 45.23% |
Reaction Steps
8-Fluoro-5-(4-methoxybenzyl)-2,5-dihydro-1H-pyrido[4,3-b]indol-1-one (I-64b: 0.15 g, 0.00046 mol) was reacted with 3-bromo-4-(trifluoromethyl)pyridine (0.13 g, 0.00058 mol), 8-hydroxy quinoline (0.016 g, 0.00011 mol), K2CO3 (0.19 g, 0.0013 mol), CuI (0.026 g, 0.00013 mol) and DMSO (3 mL) to afford the crude product. The reaction mass was cooled to room temperature, added to ammonia solution in water and extracted with ethyl acetate. The organic layer was washed with brine solution and concentrated under reduced pressure to afford the crude product. Purification by column chromatography on silica gel (1% methanol in CHCl3) afforded 95 mg of the product (45.23% yield).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08946260B2 |
| Source dataset | uspto-grants-2015_02 |
| ORD ID | ord-4b0b8a7b79fe45da8bd7e2aa29275f1a |
| Source note | uspto-grants-2015_02 |