HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 219292Generated: October 26, 2026
Water → 2-chloro-5-(1-methyl-1H-pyrazol-4-yl)nicotinonitrile
https://huagongshe.com/reaction/219292
Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | 1,4-Dioxane | HCID 31275 | — |
| Reactant | 1-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole | HCID 2773987 | — |
| Reactant | 5-Bromo-2-chloronicotinonitrile | HCID 21948269 | — |
| Catalyst | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| Product | 2-chloro-5-(1-methyl-1H-pyrazol-4-yl)nicotinonitrile | HCID 58015482 | 61.7% |
Reaction Steps
A 48 mL tube was charged with 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (8.42 g, 40.5 mmol), 5-bromo-2-chloronicotinonitrile (8.00 g, 36.8 mmol), potassium carbonate (15.3 g, 110 mmol), PdCl2(dppf) (2.69 g, 3.68 mmol), 1,4-dioxane (135 mL, 1582 mmol) and water (23.9 mL, 1324 mmol), flushed with argon, sealed and then heated to 60° C. for 8 h. The reaction mixture was concentrated, adsorbed onto silica gel, and purified via MPLC eluting with 3% MeOH in DCM. 2-chloro-5-(1-methyl-1H-pyrazol-4-yl)nicotinonitrile (4.962 g, 61.7%) was obtained (with a small impurity). The material was taken forward crude.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08198448B2 |
|---|
| Source dataset | uspto-grants-2012_06 |
|---|
| ORD ID | ord-070ec2b05bb142b9b3eb0369ee206662 |
|---|
| Source note | uspto-grants-2012_06 |
|---|
