Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | HCID 57537682 | HCID 57537682 | — |
| Catalyst | Palladium hydroxide | HCID 9942167 | — |
| Solvent | Methanol | HCID 887 | — |
| Solvent | Water | HCID 962 | — |
| Product | HCID 57537513 | HCID 57537513 | 108% |
Reaction Steps
2-{5-[4-Chloro-3-(2-methoxy-phenyl)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-pyridin-3-yl}-N,N-dimethyl-2-oxo-acetamide (57 mg, 0.129 mmol) was dissolved in methanol (7 mL), and hydrochloric acid solution was added (774 μL, 0.774 mmol, 1.0 M solution in water). The flask was purged with nitrogen gas before and after addition of Palladium hydroxide (1.8 mg, 0.013 mmol, 20 weight % on carbon, wet) The flask was purged with hydrogen gas and allowed to stir for 15 hours at 23° C. under 1 atm of hydrogen gas. The reaction mixture was filtered through Celite® and concentrated to afford 2-{5-[4-Chloro-3-(2-methoxy-phenyl)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-pyridin-3-yl}-2-hydroxy-N,N-dimethyl-acetamide (79 mg, quantitative yield) as an orange-brown oil. MS [MH+] m/z: 573.0
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08158647B2 |
|---|
| Source dataset | uspto-grants-2012_04 |
|---|
| ORD ID | ord-74b6bc4a48ed4b439b5f4ad032ded33d |
|---|
| Source note | uspto-grants-2012_04 |
|---|