HuagongsheHuagongshe Chemistry Print Report · For research reference only
Water → 2-(1-(3-cyano-4-fluorophenylsulfonyl)-2-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl)acetic acid
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Boron tribromide | HCID 25134 | — |
| Reactant | [1-(3-cyano-4-fluoro-benzenesulfonyl)-2-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl]-acetic acid methyl ester | HCID 67219319 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | 2-(1-(3-cyano-4-fluorophenylsulfonyl)-2-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl)acetic acid | HCID 11494496 | — |
Reaction Steps
1M BBr3 in CH2Cl2 (7.66 mL, 7.66 mmol) is added to a solution of [1-(3-cyano-4-fluoro-benzenesulfonyl)-2-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl]-acetic acid methyl ester (0.495 g, 1.27 mmol) in CH2Cl2 (2 mL). The reaction mixture is exposed to microwave irradiation at 60° C. for 45 minutes. Water is added to the reaction mixture which is stirred for further 20 minutes. The organic layer is isolated using the Isolute™ phase separator cartridge and evaporated. The residue is loaded on a pre-packed Isolute™ silica column and eluted using a gradient eluent from 100% CH2Cl2 to 5% methanol in CH2Cl2 to afford the title compound; MH+=374.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09169251B2 |
| Source dataset | uspto-grants-2015_10 |
| ORD ID | ord-7c6ff16633694d4da7c47fe7ca3ed177 |
| Source note | uspto-grants-2015_10 |