HuagongsheHuagongshe Chemistry Print Report · For research reference only
Sodium hydride → HCID 68504879, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | N,N-Dimethylaminoethyl chloride hydrochloride | HCID 11636816 | — |
| Reactant | Methyl 6-chloro-1H-indole-3-carboxylate | HCID 49108265 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 68504879 | HCID 68504879 | 35.6% |
Reaction Steps
To a stirred solution of 80 mg (0.38 mol) of 6-chloro-1H-indole-3-carboxylic acid methyl ester in 5 ml of DMF were added 50 mg of NaH (3 eq, 55H in oil) at RT. After 20 min, 66 mg (0.45 mmol, 1.2 eq.) of (2-chloro-ethyl)-dimethyl-amine hydrochloride were added and stirring was continued overnight at 60° C. Extraction with EtOAc/aq. NH4Cl followed by flash chromatography yielded 45 mg of crude 6-chloro-1-(2-dimethylamino-ethyl)-1H-indole-3-carboxylic acid methyl ester.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07803815B2 |
| Source dataset | uspto-grants-2010_09 |
| ORD ID | ord-24da12edf3e74f25be93752db0a3f05e |
| Source note | uspto-grants-2010_09 |