HuagongsheHuagongshe Chemistry Print Report · For research reference only
Sodium Carbonate → 3-(1-(3-fluorobenzyl)-3,5-dimethyl-1H-pyrazol-4-yl)-5-(4-(pyridin-4-yl)phenyl)-1-tosyl-1H-pyrrolo[2,3-b]pyridine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | 4-[4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]pyridine | HCID 58526497 | — |
| Reactant | 5-bromo-3-(1-(3-fluorobenzyl)-3,5-dimethyl-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridine | HCID 90031306 | — |
| Solvent | Ethanol toluene water | HCID 86587398 | — |
| Product | 3-(1-(3-fluorobenzyl)-3,5-dimethyl-1H-pyrazol-4-yl)-5-(4-(pyridin-4-yl)phenyl)-1-tosyl-1H-pyrrolo[2,3-b]pyridine | HCID 90030656 | 70.8% |
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) (150 mg, 0.27 mmol) was coupled with 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyridine (intermediate 45) (91.44 mh, 0.32 mmol) in sodium carbonate (85.86, 0.81 mmol), toluene/ethanol/water (5/5/2 ml). This afforded 120 mg (70.5% yield) of the titled compound.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09353107B2 |
| Source dataset | uspto-grants-2016_05 |
| ORD ID | ord-7d290e35be204317a0daa62004922134 |
| Source note | uspto-grants-2016_05 |