Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Pyridine | HCID 1049 | — |
| Reactant | Methanesulfonyl chloride | HCID 31297 | — |
| Reactant | HCID 86706037 | HCID 86706037 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 86706036 | HCID 86706036 | — |
Reaction Steps
A stirred solution of Intermediate 5B, 2-(3-(4-((1,5-naphthyridin-2-yl)methoxy)phenyl)-4-(pyridin-4-yl)-1H-pyrazol-1-yl)ethanol in DCM is cooled at 0° C. Pyridine (12 equivalents) and methanesulfonyl chloride (8 equivalents) are added and the reaction mixture is stirred at 0° C. for 1 h. The mixture is quenched with water and extracted with more DCM. The organic solvent is separated, dried (MgSO4), and concentrated under reduced pressure. The crude residue is purified by silica gel column chromatography. The desired fractions are collected and concentrated under reduced pressure to yield 2-(3-(4-((1,5-naphthyridin-2-yl)methoxy)phenyl)-4-(pyridin-4-yl)-1H-pyrazol-1-yl)ethyl methanesulfonate.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09138494B2 |
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| Source dataset | uspto-grants-2015_09 |
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| ORD ID | ord-237f084fea8e492db74e6a3add84a8c7 |
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| Source note | uspto-grants-2015_09 |
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