HuagongsheHuagongshe Chemistry Print Report · For research reference only
Sodium hydride → (1-carbamoyl-2-methyl-1H-indol-3-yl)-acetic acid ethyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | Chlorosulfonyl isocyanate | HCID 70918 | — |
| Reactant | Ethyl 2-methyl-3-indoleacetate | HCID 324307 | — |
| Product | (1-carbamoyl-2-methyl-1H-indol-3-yl)-acetic acid ethyl ester | HCID 68283853 | — |
Reaction Steps
The title compound was prepared in a similar manner as described in Scheme A8 Step A starting from (2-methyl-1H-indol-3-yl)-acetic acid ethyl ester [21909-49-9] (1.20 g, 5.52 mmol), NaH (60% in mineral oil, 331 mg, 8.28 mmol) and chlorosulfonylisocyanate (0.959 mL, 11.1 mmol). Purification by flash column chromatography on silica gel (EtOAc/c-hexane 1:4 to 1:1) afforded a yellowish solid. TLC, Rf (EtOAc/c-hexane 1:1)=0.31; MS: 261 [M+H]+; tR (HPLC conditions b) 3.54 min.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09085555B2 |
| Source dataset | uspto-grants-2015_07 |
| ORD ID | ord-0738f16fb56e4d67a76ba2accc8a5b19 |
| Source note | uspto-grants-2015_07 |