Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ammonia | HCID 222 | — |
| Reactant | Sodium Hydroxide | HCID 14798 | — |
| Reactant | L-Proline | HCID 145742 | — |
| Reactant | Sodium methanesulfinate | HCID 2733271 | — |
| Reactant | 5-bromo-1H-pyrrolo[2,3-b]pyridine | HCID 10307932 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Solvent | Dimethyl Sulfoxide | HCID 679 | — |
| Product | HCID 59803855 | HCID 59803855 | 50.2% |
Reaction Steps
To 5-bromo-7-azaindole (1, 1.00 g, 5.08 mmol) in dimethyl sulfoxide (15.0 mL) were added sodium methanesulfinate (0.622 g, 6.09 mmol), L-proline (0.117 g, 1.02 mmol), copper(I) iodide (0.200 g, 1.05 mmol), and sodium hydroxide (0.0406 g, 1.02 mmol). The reaction was stirred at 120° C. overnight. The reaction was poured into aqueous ammonia, and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, and filtered. The filtrate was concentrated and purified by silica gel column chromatography eluting with 20% to 100% ethyl acetate in hexane to give the desired compound as a white solid (207, 0.50 g, 50.2%). MS (ESI) [M−H+]−=195.1.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US07872018B2 |
|---|
| Source dataset | uspto-grants-2011_01 |
|---|
| ORD ID | ord-8a6fd31ff3404a07895b02af98a53221 |
|---|
| Source note | uspto-grants-2011_01 |
|---|
