HuagongsheHuagongshe Chemistry Print Report · For research reference only
Methanamine, hydrochloride (1:1) → ethyl 1-(2-(methylamino)-2-oxoethyl)-1H-indole-2-carboxylate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Methanamine, hydrochloride (1:1) | HCID 11637 | — |
| 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 | 1-(carboxy-methyl)-1H-indole-2-carboxylic ethyl ester | HCID 18327607 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | ethyl 1-(2-(methylamino)-2-oxoethyl)-1H-indole-2-carboxylate | HCID 89601817 | — |
Reaction Steps
A mixture of 2-(2-(ethoxycarbonyl)-1H-indol-1-yl)acetic acid (3.78 g), HATU (6.98 g), methylammonium chloride, and Hunig's base (6.33 mL) in DMF (77 mL) was stirred at room temperature for 24 hr. The reaction was worked up by the addition of water and the aqueous phase was extracted with EtOAc (2×65 mL). The combined organic phase was washed with brine, dried over Na2SO4, filtered and evaporated. The residue was purified by CombiFlash (0-100% EtOAc/hexane) to afford the title compound as a yellowish solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09345905B2 |
| Source dataset | uspto-grants-2016_05 |
| ORD ID | ord-289c97a6f52141fc912f358ed0430c84 |
| Source note | uspto-grants-2016_05 |