HuagongsheHuagongshe Chemistry Print Report · For research reference only
Diisopropylethylamine → 2-(5-bromo-7-fluoro-4-methoxy-1H-indol-3-yl)-N,N-dimethylacetamide
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 | 2-(5-bromo-7-fluoro-4-methoxy-1H-indol-3-yl)acetic acid | HCID 66927174 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | 2-(5-bromo-7-fluoro-4-methoxy-1H-indol-3-yl)-N,N-dimethylacetamide | HCID 66927153 | 72% |
Reaction Steps
To the solution of 8-9 (11.5 g, 38.0 mmol) in THF (300 mL) was added HATU (22.0 g, 58.0 mmol) Me2NH.HCl (3.1 g, 38.0 mmol) at 0° C. After the mixture was stirred for 5 minutes, DIPEA (12.3 g, 95.3 mmol) was added. The mixture was stirred overnight at room temperature. The volatile was removed and the residue was purified by flash chromatography (Silica gel, DCM/MeOH=50:1) to afford 8-10 (9.0 g, 72%) as white solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08912220B2 |
| Source dataset | uspto-grants-2014_12 |
| ORD ID | ord-87d18db9cf894eb8ade78e0fa66ee0c8 |
| Source note | uspto-grants-2014_12 |