HuagongsheHuagongshe Chemistry Print Report · For research reference only
Sodium Carbonate → N-(5-(3-(1-(3-fluorobenzyl)-3,5-dimethyl-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-(3-((4-methoxybenzyl)oxy)prop oxy)phenyl)methanesulfonamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | Water 1,2-dimethoxyethane | HCID 18180031 | — |
| Reactant | N-(2-(3-(4-methoxyphenoxyl)propoxy)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)methanesulfonamide | HCID 90030701 | — |
| Reactant | 5-bromo-3-(1-(3-fluorobenzyl)-3,5-dimethyl-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridine | HCID 90031306 | — |
| Product | N-(5-(3-(1-(3-fluorobenzyl)-3,5-dimethyl-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-(3-((4-methoxybenzyl)oxy)prop oxy)phenyl)methanesulfonamide | HCID 118523947 | 41% |
Reaction Steps
Using similar reaction conditions as described in step-ii of example-1, 5-bromo-3-(1-(3-fluorobenzyl)-3,5-dimethyl-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridine (step-i of example-14) (200 mg, 0.3 mmol) was coupled with N-(2-(3-(4-methoxyphenoxyl)propoxy)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)methanesulfonamide (intermediate 29) (160 mg, 0.3 mmol) in sodium carbonate (120 mg, 1 mmol) PdCl2 (dppf) (14 mg, 0.001 mmol), 1,2-dimethoxy ethane/water (2/2 mL) to afford 120 mg (41% yield) of the titled compound after purification by column (SiO2-eluted by 30% EA in hexanes).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09353107B2 |
| Source dataset | uspto-grants-2016_05 |
| ORD ID | ord-145dd0a85c5d48e8a1b0ffae15357bea |
| Source note | uspto-grants-2016_05 |