HuagongsheHuagongshe Chemistry Print Report · For research reference only
Sodium Carbonate → 2-methyl-5-(4-((4-methylpiperazin-1-yl)methyl)phenyl)-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | 4-((4-Methylpiperazin-1-yl)methyl)phenylboronic acid | HCID 45496598 | — |
| Reactant | 5-Bromo-2-methyl-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine | HCID 50987734 | — |
| Catalyst | HCID 178418476 | HCID 178418476 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Product | 2-methyl-5-(4-((4-methylpiperazin-1-yl)methyl)phenyl)-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine | HCID 86691660 | 74.1% |
Reaction Steps
1-Benzenesulfonyl-5-bromo-2-methyl-1H-pyrrolo[2,3-b]pyridine (378 mg, 1.076 mmole) and 4-((4-methylpiperazin-1-yl)methyl)phenylboronic acid (303 mg, 1.29 mmole) are dissolved in acetonitrile (10 mL) and treated with 10 mL 1 M sodium carbonate solution. To this is added 40 mg of PdCl2(PPh3)2 catalyst, and the mixture is irradiated for 5 minutes at 150 degrees in a Biotage microwave reactor. After cooling, the reaction mixture is diluted with water and extracted with ethyl acetate, dried, and concentrated. MPLC silica gel chromotagraphy 5-20% MeOH in dichloromethane gradient elution, provided 367 mg of the title compound as a solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08846909B2 |
| Source dataset | uspto-grants-2014_09 |
| ORD ID | ord-c6c47da688594eaea5cf625797af4a36 |
| Source note | uspto-grants-2014_09 |