Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sodium Acetate | HCID 517045 | — |
| Reactant | (2-(7,7-dimethyl-1-oxo-3,4,7,8-tetrahydro-1H-cyclopenta[4,5]pyrrolo[1,2-a]pyrazin-2(6H)-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-yl)methyl acetate | HCID 86684419 | — |
| Reactant | HCID 86684612 | HCID 86684612 | — |
| Catalyst | Water | HCID 962 | — |
| Catalyst | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Product | HCID 86684613 | HCID 86684613 | 52.4% |
Reaction Steps
A 50-mL single-neck round-bottomed flask equipped with a magnetic stirrer and a reflux condenser was charged with 337d (20 mg, 0.67 mmol), {3-[(acetoxy)methyl]-2-{4,4-dimethyl-9-oxo-1,10-diazatricyclo[6.4.0.02,6]dodeca-2(6),7-dien-10-yl}pyridin-4-yl}boronic acid 199e (270 mg, 0.67 mmol), Pd(dppf)Cl2 (42 mg, 0.050 mmol), sodium acetate (82 mg, 1.0 mmol), K3PO4 trihydrate (266 mg, 1.0 mmol), water (6 drops), and acetonitrile (6 mL). After three cycles of vacuum/nitrogen flush, the mixture was heated at 95° C. for 2 h. It was then filtered and the filtrate was evaporated under reduced pressure. The residue was purified by silica-gel column chromatography eluting with 25:1 dichloromethane/methanol to afford 337e (200 mg, 50%) as a brown solid. LCMS-ESI: [M+H]+ 570.3
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US09238655B2 |
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| Source dataset | uspto-grants-2016_01 |
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| ORD ID | ord-3d6a6735ba154b2fb7c5af5dd171e7ef |
|---|
| Source note | uspto-grants-2016_01 |
|---|
