Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Pyridine | HCID 1049 | — |
| Reactant | Methanesulfonyl chloride | HCID 31297 | — |
| Reactant | HCID 86681636 | HCID 86681636 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 86681638 | HCID 86681638 | 86.3% |
Reaction Steps
To a suspension of ethyl 2-(3-amino-1H-indol-1-yl)acetate hydrochloride (220 mg, 0.864 mmol) in dry DCM (4 ml), cooled at 0° C. under nitrogen, methanesulfonyl chloride (67.3 μl, 0.864 mmol) and dry pyridine (559 μl, 6.91 mmol) were added. After stirring at 0° C. for 4 hours, the mixture was partitioned between 5% aqueous citric acid and DCM; the organic phase was washed with water, dried over Na2SO4 and evaporated to give ethyl 2-(3-(methylsulfonamido)-1H-indol-1-yl)acetate (221 mg, 0.746 mmol, 86% yield). MS/ESI+ 319.0 [MNa]+. This product was used in the next step without any additional purification.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09024027B2 |
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| Source dataset | uspto-grants-2015_05 |
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| ORD ID | ord-56b602615acf472cb446fb9d1847bbf8 |
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| Source note | uspto-grants-2015_05 |
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