HuagongsheHuagongshe Chemistry Print Report · For research reference only
Dimethylformamide → n-((5-Chloro-1h-indol-3-yl)methyl)-5-(3-fluorobenzyl)isoxazole-3-carboxamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Dimethylformamide | HCID 6228 | — |
| Reactant | Ethyl Acetate | HCID 8857 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) | HCID 9886157 | — |
| Reactant | (5-Chloro-1H-indol-3-yl)methanamine | HCID 21281458 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | n-((5-Chloro-1h-indol-3-yl)methyl)-5-(3-fluorobenzyl)isoxazole-3-carboxamide | HCID 66831683 | 22% |
Reaction Steps
This compound was prepared following Method A starting from (5-chloro-1H-indol-3-yl)methanamine (0.060 g; 0.332 mmol), the intermediate 11 (0.081 g; 0.365 mmol), HATU (0.139 g; 0.365 mmol) and N,N-diisopropylethylamine (0.075 mL; 0.432 mmol) in DMF (5 mL). Flash chromatography on silica gel eluting with 2 to 10% of ethyl acetate in dichloromethane afforded 0.028 g (22%) of N-((5-chloro-1H-indol-3-yl)methyl)-5-(3-fluorobenzyl)isoxazole-3-carboxamide as a solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08618138B2 |
| Source dataset | uspto-grants-2013_12 |
| ORD ID | ord-d67c27a9d7914461bb9d952f5a5a2ba7 |
| Source note | uspto-grants-2013_12 |