Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Methyl iodide | HCID 6328 | — |
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | HCID 77105958 | HCID 77105958 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 77105959 | HCID 77105959 | 19.3% |
Reaction Steps
To a solution of 5-(3-methoxyphenyl)-3-[5-(4-piperidyl)-1,3,4-oxadiazol-2-yl]pyridin-2-amine (150 mg, 0.42 mmol) in THF (20 mL) was added 60% NaH (25.0 mg, 064 mmol) at 0° C. and the reaction mixture was stirred at 0° C. for 10 min. Then MeI (54.5 mg, 0.38 mmol) was added at 0° C. and stirred the reaction mixture at 0° C. for 2 h. The reaction mixture was poured into ice-water (30 mL), extracted with ethyl acetate (3×20 mL), organic layer was washed with brine, dried over anhydrous sodium sulphate and concentrated under reduced pressure. Crude product was purified by preparative TLC to afford the title compound as a yellow solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US09321748B2 |
|---|
| Source dataset | uspto-grants-2016_04 |
|---|
| ORD ID | ord-3246b2ca5dc643d297a006a03a3d31eb |
|---|
| Source note | uspto-grants-2016_04 |
|---|