HuagongsheHuagongshe Chemistry Print Report · For research reference only
Boron trifluoride etherate → N-(4-chloro-5-methyl-3-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-5-methyl-3-isoxazolyl)-N-(methoxyethoxymethyl)-2-[alpha-hydroxy-2-methyl-4,5-(methylenedioxy)-benzyl]thieno[2,3-b]pyridine-3-sulfonamid | HCID 18614043 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | N-(4-chloro-5-methyl-3-isoxazolyl)-N-(methoxyethoxymethyl)-2-[2-methyl-4,5-(methylenedioxy)benzyl]thieno[2,3-b]pyridine-3-sulfonamide | HCID 18614045 | 53.9% |
Reaction Steps
The title compound was prepared by the method of Example 5(A) using N-(4-chloro-5-methyl-3-isoxazolyl)-N-(methoxyethoxymethyl)-2-[α-hydroxy-2-methyl-4,5-(methylenedioxy)benzyl]thieno[2,3-b]pyridine-3-sulfonamide (0.11 g, 0.19 mmoles), CH2Cl2 (5 ml), triethyl silane (0.31 ml, 1.9 mmoles) and boron trifluoride etherate (0.12 ml, 0.97 mmoles). Flash chromatography (35% EtOAc/hexanes) provided 58 mg (53%) of the title compound as a tan solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06329387B2 |
| Source dataset | uspto-grants-2001_12 |
| ORD ID | ord-7963ebe0261848b49008682e69c048b3 |
| Source note | uspto-grants-2001_12 |