Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | 1,2-Diaminocyclohexane, (+)- | HCID 479307 | — |
| Reactant | 3-Bromopyridine-4-carboxaldehyde | HCID 2762997 | — |
| Reactant | 6-Chloro-3,4-dihydroisoquinolin-1(2H)-one | HCID 19375637 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | HCID 86685987 | HCID 86685987 | 348.8% |
Reaction Steps
CuI (190 mg, 1 mmol), (1S,2S)-cyclohexane-1,2-diamine (228 mg, 2 mmol) and Cs2CO3 (6.5 g, 20 mmol) were added to a solution of 6-chloro-3,4-dihydro-2H-isoquinolin-1-one (1.82 g, 10 mmol, intermediate A-2) and 5-bromo-pyridine-4-carbaldehyde (3.72 g, 20 mmol) in dioxane (15 mL). The reaction mixture was heated to 150° C. using microwave for 2.5 hours before it was poured into H2O (50 mL) and extracted with EtOAc (2×20 mL). The organic layers were washed with brine, dried over anhy. Na2SO4, filtered and concentrated in vacuo to give a crude product (2.0 g, 70%) as brown oil. MS: 287.0 (M+H+).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US09133158B2 |
|---|
| Source dataset | uspto-grants-2015_09 |
|---|
| ORD ID | ord-58b16153334a4180bd69e23a0e1eb83c |
|---|
| Source note | uspto-grants-2015_09 |
|---|
