HuagongsheHuagongshe Chemistry Print Report · For research reference only
Boron trifluoride etherate → N-(4-chloro-3-methyl-5-isoxazolyl)-N-(methoxyethoxymethyl)-2-[2-methyl-4,5-(methylenedioxy)benzyl]thieno[2,3-b]pyridine-3-sulfonamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Boron trifluoride etherate | HCID 8000 | — |
| Reactant | Triethylsilane | HCID 12052 | — |
| Reactant | N-(4-chloro-3-methyl-5-isoxazolyl)-N-(methoxyethoxymethyl)-2-[alpha-hydroxy-2-methyl-4,5-(methylenedioxy)-benzyl]thieno [2,3-b]pyridine-3-sulfonamide | HCID 18614054 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | N-(4-chloro-3-methyl-5-isoxazolyl)-N-(methoxyethoxymethyl)-2-[2-methyl-4,5-(methylenedioxy)benzyl]thieno[2,3-b]pyridine-3-sulfonamide | HCID 53756172 | 82% |
Reaction Steps
The title compound was prepared by the method of Example 5(A), using N-(4-chloro-3-methyl-5-isoxazolyl)-N-(methoxyethoxymethyl)-2-[α-hydroxy-2-methyl-4,5-(methylenedioxy)benzyl]thieno[2,3-b]pyridine-3-sulfonamide (0.16 g, 0.28 mmoles), CH2Cl2 (3 ml), triethylsilane (0.45 ml, 2.8 mmoles) and boron trifluoride etherate (0.17 ml, 1.4 mmoles). Flash chromatography (40% EtOAc/hexanes) provided 0.13 g (82%) of the title compound.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06329387B2 |
| Source dataset | uspto-grants-2001_12 |
| ORD ID | ord-195a485cb44e4b048c55225900a3801c |
| Source note | uspto-grants-2001_12 |