Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ethyl Acetate | HCID 8857 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | 3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine | HCID 2734656 | — |
| Reactant | HCID 117667266 | HCID 117667266 | — |
| Catalyst | Bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II) | HCID 11714597 | — |
| Solvent | 1,4-Dioxane--water (1/1) | HCID 21886435 | — |
| Product | HCID 86305809 | HCID 86305809 | 44.3% |
Reaction Steps
A mixture of 6-bromo-4,4-difluoro-3,4-dihydro-2H [1,8]naphthyridine-1-carboxylic acid amide (89.6 mg, 0.31 mmol), 3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-pyridine (92.3 mg, 0.46 mmol), K2CO3 (105 mg, 0.77 mmol) and bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium (II) (21.8 mg, 0.03 mmol) in 1 mL dioxane/water (9:1) is heated at 100° C. for 2 hrs. 30 mL of EtOAc is added. The mixture is washed with 2×10 mL of NaHCO3 and 1×10 mL brine. The organic phase is dried with MgSO4, filtered and concentrated. The residue is applied to a silica preparative TLC plate and purified (10% MeOH/CH2Cl2) to give 39.9 mg of the titled product.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US09181272B2 |
|---|
| Source dataset | uspto-grants-2015_11 |
|---|
| ORD ID | ord-ca71927872e3427680ddda2f255566fa |
|---|
| Source note | uspto-grants-2015_11 |
|---|
