Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | (4-Ethynylphenyl)boronic acid | HCID 23436919 | — |
| Reactant | (S)-tert-butyl 2-(5-iodo-1H-imidazol-2-yl)pyrrolidine-1-carboxylate | HCID 58498756 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Catalyst | HCID 178418397 | HCID 178418397 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 58516265 | HCID 58516265 | 72.9% |
Reaction Steps
Nitrogen was bubbled through a solution of (S)-tert-butyl 2-(5-iodo-1H-imidazol-2-yl)pyrrolidine-1-carboxylate (150 mg, 0.41 mmol), 4-ethynylphenylboronic acid (90 mg, 0.62 mmol) and copper(I) iodide (15.7 mg, 0.083 mmol) in DMF (5 mL) and triethylamine (0.30 mL, 2.0 mmol) for 15 min. Then Pd(PPh3)4 (23.86 mg, 0.021 mmol) was added and the reaction mixture was vacuum flushed with nitrogen (4×,), sealed and heated at 60° C. ON. The crude reaction was concentrated to dryness, dissolved into DMF/MeOH and purified by Prep HPLC (MeOH/water with ammonium acetate buffer) to yield (S)-4-((2-(1-(tert-butoxycarbonyl)pyrrolidin-2-yl)-1H-imidazol-5-yl)ethynyl)phenylboronic acid (113.8 mg, 0.299 mmol) as a light yellow solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08618153B2 |
|---|
| Source dataset | uspto-grants-2013_12 |
|---|
| ORD ID | ord-b805775a0c66431b85070c61ab855b25 |
|---|
| Source note | uspto-grants-2013_12 |
|---|
