HuagongsheHuagongshe Chemistry Print Report · For research reference only
Ethyl chloroformate → HCID 57619241, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Ethyl chloroformate | HCID 10928 | — |
| Reactant | 1H-Pyrrolo[2,3-b]pyridine-1-carboxylic acid, 5-chloro-3-[(dimethylamino)methyl]-, 1,1-dimethylethyl ester | HCID 57619203 | — |
| Solvent | Toluene | HCID 1140 | — |
| Product | HCID 57619241 | HCID 57619241 | 39.1% |
Reaction Steps
To 5-chloro-3-dimethylaminomethyl-pyrrolo[2,3-b]pyridine-1-carboxylic acid tert-butyl ester (141, 4.20 g, 13.6 mmol) in 100 mL of toluene, ethyl chloroformate (1.48 mL, 15.5 mmol) was added under nitrogen. The reaction was stirred at room temperature for 2 hours, then concentrated under vacuum and combined with water and extracted with ethyl acetate. The organic layer was dried over sodium sulfate, filtered and the filtrate was concentrated under vacuum. The resulting material was purified by silica gel column chromatography eluting with 25% ethyl acetate in hexane to provide the desired compound (142, 1.60 g).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09096593B2 |
| Source dataset | uspto-grants-2015_08 |
| ORD ID | ord-6c6e68c7889b4080a3e4562844effcd1 |
| Source note | uspto-grants-2015_08 |