HuagongsheHuagongshe Chemistry Print Report · For research reference only
Potassium Carbonate → 5-[5-(hydroxymethyl)-2-thienyl]-3-(1-{[3-(1-pyrrolidinyl)propyl]sulfonyl}-4-piperidinyl)-1H-indole-7-carboxamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | 5-HYDROXYMETHYLTHIOPHENE-2-BORONIC ACID | HCID 4374265 | — |
| Reactant | 3-(1-{[2-(1-pyrrolidinyl)ethyl]sulfonyl}-4-piperidinyl)-5-(3-thienyl)-1H-indole-7-carboxamide | HCID 11620053 | — |
| Reactant | 5-bromo-3-(1-{[3-(1-pyrrolidinyl)propyl]sulfonyl}-4-piperidinyl)-1H-indole-7-carboxamide | HCID 59003300 | — |
| Catalyst | HCID 178418397 | HCID 178418397 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | 5-[5-(hydroxymethyl)-2-thienyl]-3-(1-{[3-(1-pyrrolidinyl)propyl]sulfonyl}-4-piperidinyl)-1H-indole-7-carboxamide | HCID 11620724 | — |
Reaction Steps
The title compound was prepared following the general procedure described in intermediate 16. Thus, 5-bromo-3-(1-{[3-(1-pyrrolidinyl)propyl]sulfonyl}-4-piperidinyl)-1H-indole-7-carboxamide (95 mg, 0.19 mmol) in dioxane (3 mL) and water (1 mL), [5-(hydroxymethyl)-2-thienyl]boronic acid (120 mg, 0.76 mmol), Pd(PPh3)4 (22.2 mg, 10%) and potassium carbonate (211 mg, 1.52 mmol) were reacted to form the desired product which was purified by flash column chromatography (ethyl acetate/hexane, 1/1) to yield the desired product (25 mg, 25%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07858796B2 |
| Source dataset | uspto-grants-2010_12 |
| ORD ID | ord-d640780688ef4d46a97e0586f55d1647 |
| Source note | uspto-grants-2010_12 |