Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Quinoxaline | HCID 7045 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | 9-Borabicyclo(3.3.1)nonane | HCID 78966 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | 2-Methylidenepiperidine | HCID 17803143 | — |
| Reactant | HCID 178514824 | HCID 178514824 | — |
| Solvent | N,N-Dimethylformamide--water (1/1) | HCID 21962138 | — |
| Product | Quinazoline | HCID 9210 | — |
Reaction Steps
Methylene piperidine ED.8 (243 mg, 1.23 mmol) is combined with 9-BBN (2.46 mL, 0.5 M in THF) and heated to 65° C. for 1 h. Then the mixture is cooled to 20° C., quinoxaline D*.5 (300 mg, 1.23 mmol), Pd(dppf) (50 mg, 10 mol %) and K2CO3 (195 mg, 1.41 mmol) are placed in DMF/H2O (1.2 mL, 5:1) and slowly the freshly prepared boronate is added dropwise. The reaction mixture is heated to 60° C. for 2 h, cooled, combined with NaHCO3 and extracted with DCM (3×10 mL). The solvent is removed, the residue is purified by chromatography (45:55 to 90:10 in 6 min CH3CN/H2O) and quinoxaline D.51 (250 mg, 50%) is obtained.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08575203B2 |
|---|
| Source dataset | uspto-grants-2013_11 |
|---|
| ORD ID | ord-1965449d750b499da13f2a9318354e43 |
|---|
| Source note | uspto-grants-2013_11 |
|---|
