Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Bromide ion | HCID 259 | — |
| Reactant | Potassium Phosphate, Tribasic | HCID 62657 | — |
| Reactant | N-(5-(2,2-difluoro-6-methylbenzo[d][1,3]dioxol-5-yl)pyrazin-2-yl)-2-fluorobenzamide | HCID 58486754 | — |
| Reactant | Dioxane acetonitrile water | HCID 67448433 | — |
| Product | HCID 58486878 | HCID 58486878 | 76% |
Reaction Steps
Palladium tetrakis-triphenylphosphine (68 mg, 0.1 mmol) was added to a degassed solution of bromide 244 (250 mg, 1.2 mmol) and boronate 11 (521 mg, 2.4 mmol) in dioxane: acetonitrile:water (9:9:2, 6 mL) and potassium phosphate (376 mg, 1.8 mmol). The resulting mixture was heated under argon at 90° C. with stiffing for 18 hours. The mixture was then cooled, extracted with dichloromethane (3×15 mL), dried with sodium sulfate and concentrated under reduced pressure. Flash chromatography (ISCO system, silica, 0-50% ethyl acetate in hexane) provided 245 (202 mg, 76%) as an solid: LRESIMS m/z 225.2 [M+H]+, calcd. for C14H13N2O1 225.1.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US09120751B2 |
|---|
| Source dataset | uspto-grants-2015_09 |
|---|
| ORD ID | ord-3d027ff7cd7e4cf0b9de3242a764583e |
|---|
| Source note | uspto-grants-2015_09 |
|---|
