HuagongsheHuagongshe Chemistry Print Report · For research reference only
1,2-Dichloroethane → 2-Bromo-N-methyl-N-[(1-methyl-1H-indol-2-yl)methyl]benzamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 1,2-Dichloroethane | HCID 11 | — |
| Reactant | Water | HCID 962 | — |
| Reactant | 2-Bromobenzoic acid | HCID 6940 | — |
| Reactant | 1-Hydroxybenzotriazole | HCID 75771 | — |
| Reactant | methyl((1-methyl-1H-indol-2-yl)methyl)amine | HCID 11401058 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | 2-Bromo-N-methyl-N-[(1-methyl-1H-indol-2-yl)methyl]benzamide | HCID 22722078 | 63% |
Reaction Steps
EDC (660 mg, 3.44 mmole) was added to a solution of 2-bromobenzoic acid (693 mg, 3.45 mmole), 1-methyl-2-(methylaminomethyl)indole (600 mg, 3.45 mmole), and HOBt.H2O (466 mg, 3.45 mmole) in DMF at RT. The reaction was stirred overnight, then was concentrated in vacuo. The residue was diluted with 5% NaHCO3 and extracted with CH2Cl2. The combined organic extracts were washed with brine and dried over MgSO4. Flash chromatography on silica gel (2% MeOH/CH2Cl2) gave the title compound (750 mg, 63%): MS (ES) m/e 357 (M+H)+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06730684B1 |
| Source dataset | uspto-grants-2004_05 |
| ORD ID | ord-ee8a0ba7b78a4b0da7a549a14e2d8c43 |
| Source note | uspto-grants-2004_05 |