HuagongsheHuagongshe Chemistry Print Report · For research reference only
Sodium Carbonate → Tert-butyl 4-(1-[5-(3-aminophenyl)-1,3-thiazol-2-yl]-1-hydroxyethyl)piperidine-1-carboxylate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | 3-Aminophenylboronic acid monohydrate | HCID 14389423 | — |
| Reactant | Tert-butyl 4-[1-(5-bromo-1,3-thiazol-2-yl)-1-hydroxyethyl]piperidine-1-carboxylate | HCID 67431988 | — |
| Catalyst | HCID 178418397 | HCID 178418397 | — |
| Solvent | 1,2-Dimethoxyethane | HCID 8071 | — |
| Product | Tert-butyl 4-(1-[5-(3-aminophenyl)-1,3-thiazol-2-yl]-1-hydroxyethyl)piperidine-1-carboxylate | HCID 67433207 | 92% |
Reaction Steps
The product of Step 2 (87 mg, 0.222 mmol), 3-aminophenylboronic acid monohydrate (41.3 mg, 0.267 mmol), Pd(Ph3P)4 (12.85 mg, 0.011 mmol) and Na2CO3 (0.333 mL, 0.667 mmol) were stirred in DME at 100° C. overnight under N2. The reaction mixture was filtered through a pre-pack pad of celica with dichloromethane. The filtrate was concentrated and the residue was purified by flash chromatography to give tert-butyl 4-{1-[5-(3-aminophenyl)-1,3-thiazol-2-yl]-1-hydroxyethyl}piperidine-1-carboxylate (82.4 mg, 0.204 mmol, 92%) as a yellow oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08551984B2 |
| Source dataset | uspto-grants-2013_10 |
| ORD ID | ord-b935c3502d6c40d3b424907c9634c076 |
| Source note | uspto-grants-2013_10 |