HuagongsheHuagongshe Chemistry Print Report · For research reference only
1,2-Dichloroethane → (E)-3-(6-aminopyridin-3-yl)-N-(1H-indol-3-ylmethyl)-N-methylacrylamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 1,2-Dichloroethane | HCID 11 | — |
| Reactant | Water | HCID 962 | — |
| Reactant | 1-Hydroxybenzotriazole | HCID 75771 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | (2E)-3-(6-aminopyridin-3-yl)prop-2-enoic acid | HCID 10487224 | — |
| Reactant | 1-Acetyl-3-(methylaminomethyl)indole | HCID 22139040 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | (E)-3-(6-aminopyridin-3-yl)-N-(1H-indol-3-ylmethyl)-N-methylacrylamide | HCID 10018036 | 59.3% |
Reaction Steps
EDC (1.03 g, 5.40 mmole) was added to a solution of (E)-3-(6-aminopyridin-3-yl)acrylic acid (0.89 g, 5.40 mmole), 1-acetyl-3-(methylaminomethyl)indole (1.00 g, 4.95 mmole), HOBt.H2O (0.73 g.,5.40 mmole) and diisopropylethylamine (1.72 mL, 9.90 mmole) in DMF (50 mL) at RT. The reaction was stirred overnight then was concentrated in vacuo. The residue was diluted with water and extracted with ethyl acetate. The combined organic extracts were washed with brine and dried over Na2SO4. Flash chromatography on silica gel (5% MeOH/CHCl3) gave the title compound (0.90 g, 52%) as a light yellow solid after drying in vacuo: MS (ES) m/e 307 (M+H)+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07049310B2 |
| Source dataset | uspto-grants-2006_05 |
| ORD ID | ord-f81e0f0fc5b342a6834af3f729d7f0af |
| Source note | uspto-grants-2006_05 |