HuagongsheHuagongshe Chemistry Print Report · For research reference only
Dimethylformamide → 4-((1-(1,3-Difluoropropan-2-yl)-4-fluoropiperidin-4-yl)methoxy)-3-nitrobenzenesulfonamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Dimethylformamide | HCID 6228 | — |
| Reactant | 1,3-Difluoroacetone | HCID 228397 | — |
| Reactant | Sodium triacetoxyborohydride | HCID 5049666 | — |
| Reactant | 4((4-Fluoropiperidin-4-yl)methoxy)-3-nitrobenzenesulfonamide | HCID 67126502 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | 4-((1-(1,3-Difluoropropan-2-yl)-4-fluoropiperidin-4-yl)methoxy)-3-nitrobenzenesulfonamide | HCID 67422931 | — |
Reaction Steps
To a suspension of EXAMPLE 341C (0.100 g) and 1,3-difluoropropan-2-one (0.025 g) in dichloromethane (2 mL) was added sodium triacetoxyborohydride (0.071 g). After 15 minutes, N,N-dimethylformamide was added dropwise until an orange solution resulted (˜15 drops). After stirring overnight additional 1,3-difluoropropan-2-one and sodium triacetoxyborohydride were added. After 3 hours, the reaction was loaded onto silica gel (Reveleris 40 g) and eluted with a gradient of 0.5-5% methanol/dichloromethane over 30 minutes (flow=40 ml/minutes) to provide the title compound.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09303025B2 |
| Source dataset | uspto-grants-2016_04 |
| ORD ID | ord-e17380d93f4348208470ae62ce780259 |
| Source note | uspto-grants-2016_04 |