HuagongsheHuagongshe Chemistry Print Report · For research reference only
HCID 59146119, compound → HCID 59146036, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | HCID 59146119 | HCID 59146119 | — |
| Reactant | HCID 178418546 | HCID 178418546 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 59146036 | HCID 59146036 | 74.3% |
Reaction Steps
To a suspension of ethyl 3-(5-bromo-7-fluoro-1H-indol-2-yl)propanoate (D161) (650 mg), copper(I) iodide (394 mg) in DMF (5 mL) was added copper(I) cyanide (741 mg). The reaction vessel was sealed and heated in Biotage Initiator using initial very high to 200° C. for an hour. After cooling the reaction, the precipitate was filtered, and the filtrate was diluted with EtOAc (30 mL). The organic phase was washed with brine (25 mL), water (25 mL×2). The organic layer was dried over sodium sulphate and the crude product was purified by column chromatography to give ethyl 3-(5-cyano-7-fluoro-1H-indol-2-yl)propanoate (D162) (400 mg) as a yellow solid. MS (ES): C14H13FN2O2 requires 260; found 261.1 (M+H+).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08217028B2 |
| Source dataset | uspto-grants-2012_07 |
| ORD ID | ord-ad0f3e39703f401daaacf490a806ba47 |
| Source note | uspto-grants-2012_07 |