HuagongsheHuagongshe Chemistry Print Report · For research reference only
m-Chloroperbenzoic acid → 5-fluoro-3-(4-(methylsulfinyl)pyrimidin-2-yl)-1-trityl-1H-pyrazolo[3,4-b]pyridine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | m-Chloroperbenzoic acid | HCID 70297 | — |
| Reactant | 5-Fluoro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-trityl-1H-pyrazolo[3,4-b]pyridine | HCID 67975717 | — |
| Reactant | 5-fluoro-3-(4-(methylthio)pyrimidin-2-yl)-1-trityl-1H-pyrazolo[3,4-b]pyridine | HCID 71247968 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | 5-fluoro-3-(4-(methylsulfinyl)pyrimidin-2-yl)-1-trityl-1H-pyrazolo[3,4-b]pyridine | HCID 71247494 | — |
Reaction Steps
To a cold (0° C.) mixture of 5-fluoro-3-(4-(methylthio)pyrimidin-2-yl)-1-trityl-1H-pyrazolo[3,4-b]pyridine, 135a, (0.70 g, 1.38 mmol) in dichloromethane (10.4 mL) was added mCPBA (0.43 g, 1.93 mmol). After 30 minutes, the mixture was diluted with dichloromethane and washed with 2N NaOH and brine. The organic phase was brine dried over Na2SO4, filtered and stripped down twice with CH3CN to afford 660 mg of desired product that was used without further purification: LCMS Gradient 60-98%, 0.1% formic acid, 7 min, C4/ACN, Retention Time=2.68 minutes (M+H) 520.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09051319B2 |
| Source dataset | uspto-grants-2015_06 |
| ORD ID | ord-4e3bc2bf7f0942af90471c6860bf9654 |
| Source note | uspto-grants-2015_06 |