HuagongsheHuagongshe Chemistry Print Report · For research reference only
Diisopropylethylamine → 3-(3-fluorobenzyl)-N-(4-(trimethylsilyl)but-3-ynyl)benzamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| 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 | (4-Aminobut-1-yn-1-yl)trimethylsilane | HCID 19703099 | — |
| Reactant | HCID 67974126 | HCID 67974126 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | 3-(3-fluorobenzyl)-N-(4-(trimethylsilyl)but-3-ynyl)benzamide | HCID 67974665 | 42.3% |
Reaction Steps
A mixture of 4-(trimethylsilyl)but-3-yn-1-amine (0.184; 1.30 mmol), 3-(3-fluorobenzyl)benzoic acid, (0.200 g; 0.869 mmol), HATU (0.363 g; 0.955 mmol) and N,N-diisopropylethylamine (0.374 mL; 2.17 mmol) in DMF (20 mL) was stirred at room temperature for 18 hours and concentrated under reduced pressure. The residue was dissolved in ethyl acetate and the organic layer was washed with water, dried and concentrated under reduced pressure. The crude material was purified by flash chromatography on silica gel (eluent 20 to 100% ethyl acetate in heptane) to afford 0.13 g (42%) of 3-(3-fluorobenzyl)-N-(4-(trimethylsilyl)but-3-ynyl)benzamide which was used without further purification.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09266832B2 |
| Source dataset | uspto-grants-2016_02 |
| ORD ID | ord-2fbd499dd21c46d4bac2b057a5cdf548 |
| Source note | uspto-grants-2016_02 |