Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Methanesulfonyl chloride | HCID 31297 | — |
| Reactant | HCID 71284985 | HCID 71284985 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 89422916 | HCID 89422916 | 98.7% |
Reaction Steps
To solution of methyl 1-(2,4-dimethoxybenzyl)-5-ethyl-6-(2-(2-hydroxyethyl)-1-methyl-1H-indol-5-yl)-2-oxo-1,2-dihydropyridine-3-carboxylate (1.142 g, 2.26 mmol) in DCM (10 mL) was added NEt3 (0.45 mL, 3.23 mmol) and mixture was cooled to 0° C. Methanesulfonyl chloride (0.22 mL, 2.84 mmol) was added dropwise and reaction mixture was stirred at 0° C. 15 min. LC/MS indicated complete consumption of the starting material. Reaction was diluted with DCM (20 mL) and washed with H2O (10 mL). Organic phase was dried over Na2SO4 and solvent was removed under reduced pressure. Methyl 1-(2,4-dimethoxybenzyl)-5-ethyl-6-(1-methyl-2-(2-(methylsulfonyloxy)ethyl)-1H-indol-5-yl)-2-oxo-1,2-dihydropyridine-3-carboxylate (1.30 g) was obtained in nearly quantitative yield as yellow solid and was pure enough to be used in the next step without purification.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09409905B2 |
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| Source dataset | uspto-grants-2016_08 |
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| ORD ID | ord-0aa894561659414b9d6a9217d68655f4 |
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| Source note | uspto-grants-2016_08 |
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