HuagongsheHuagongshe Chemistry Print Report · For research reference only
Cesium carbonate → 3-(1-{[3-(dimethylamino)propyl]sulfonyl}-4-piperidinyl)-5-[3-(hydroxymethyl)phenyl]-1H-indole-7-carboxamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | [3-(Hydroxymethyl)phenyl]boronic acid | HCID 2734662 | — |
| 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-(dimethylamino)propyl]sulfonyl}-4-piperidinyl)-1H-indole-7-carboxamide | HCID 59003361 | — |
| Catalyst | HCID 178418397 | HCID 178418397 | — |
| Product | 3-(1-{[3-(dimethylamino)propyl]sulfonyl}-4-piperidinyl)-5-[3-(hydroxymethyl)phenyl]-1H-indole-7-carboxamide | HCID 11605713 | — |
Reaction Steps
The title compound was prepared following the general procedure described in intermediate 16. Thus, 5-bromo-3-(1-{[3-(dimethylamino)propyl]sulfonyl}-4-piperidinyl)-1H-indole-7-carboxamide (150 mg, 0.32 mmol), [3-(hydroxymethyl)phenyl]boronic acid (195 mg, 1.27 mmol), Pd(PPh3)4 (31 mg, 10%) and cesium carbonate (220 mg, 0.64 mmol) 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 yield the desired product (230.0 mg, 36%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07858796B2 |
| Source dataset | uspto-grants-2010_12 |
| ORD ID | ord-bd7e866203894a1a9680b38e2b74d4b7 |
| Source note | uspto-grants-2010_12 |