HuagongsheHuagongshe Chemistry Print Report · For research reference only
Potassium Carbonate → 5-(5-chloro-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 | 1,4-Dioxane | HCID 31275 | — |
| Reactant | 5-Chlorothiophene-2-boronic acid | HCID 2734324 | — |
| Reactant | 3-(1-{[2-(1-pyrrolidinyl)ethyl]sulfonyl}-4-piperidinyl)-5-(3-thienyl)-1H-indole-7-carboxamide | HCID 11620053 | — |
| Catalyst | HCID 178418397 | HCID 178418397 | — |
| Solvent | Water | HCID 962 | — |
| Product | 5-(5-chloro-2-thienyl)-3-(1-{[3-(1-pyrrolidinyl)propyl]sulfonyl}-4-piperidinyl)-1H-indole-7-carboxamide | HCID 11504754 | — |
Reaction Steps
The title compound was prepared following the general procedure described in intermediate 16. Thus, 15-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-chloro-2-thienylboronic acid (123 mg, 0.76 mmol), Pd(PPh3)4 (22.2 mg, 10%) and potassium carbonate (211 mg, 1.52 mmol) in dioxane (3.0 mL) and water (1.0 mL) were reacted to form the desired product which was purified by reverse phase HPLC eluting with 10% B to 80% B, where A=H2O (0.1% trifluoroacetic acid) and B=CH3CN (0.1% trifluoroacetic acid) to give the title compound (11 mg, 11%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07858796B2 |
| Source dataset | uspto-grants-2010_12 |
| ORD ID | ord-8d29cd79ba3c4f86a1efb03bb449f4bd |
| Source note | uspto-grants-2010_12 |