HuagongsheHuagongshe Chemistry Print Report · For research reference only
Cesium carbonate → 5-(5-formyl-3-thienyl)-3-{1-[(1-methylethyl)sulfonyl]-4-piperidinyl}-1H-indole-7-carboxamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | 4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)thiophene-2-carbaldehyde | HCID 46739783 | — |
| Reactant | 5-bromo-3-{1-[(1-methylethyl)sulfonyl]-4-piperidinyl}-1H-indole-7-carboxamide | HCID 57732627 | — |
| Catalyst | HCID 178418397 | HCID 178418397 | — |
| Product | 5-(5-formyl-3-thienyl)-3-{1-[(1-methylethyl)sulfonyl]-4-piperidinyl}-1H-indole-7-carboxamide | HCID 57732783 | 86% |
Reaction Steps
A solution of 5-bromo-3-{1-[(1-methylethyl)sulfonyl]-4-piperidinyl}-1H-indole-7-carboxamide (428 mg, 1 mmol), 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-thiophenecarbaldehyde (960 mg, 4 mmol), Cs2CO3 (800 mg, 2.46 mmol), and Pd(PPh3)4 (100 mg, 0.0865 mmol) were heated in a Smith microwave at 160° C. for 20 min. The reaction mixture was filtered and concentrated under reduced pressure. The crude product was washed with MeOH (1×5 mL) to give the title compound (395 mg, 86%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08354406B2 |
| Source dataset | uspto-grants-2013_01 |
| ORD ID | ord-ff074b376a784b24aa484ca3326a5548 |
| Source note | uspto-grants-2013_01 |