HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1623260Generated: November 1, 2026
Dichloromethane → 4-(((5'-chloro-2'-fluoro-[2,4'-bipyridin]-6-yl)amino)methyl)tetrahydro-2H-pyran-4-carbonitrile
https://huagongshe.com/reaction/1623260
Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Dichloromethane | HCID 6344 | — |
| Reactant | (5-Chloro-2-fluoropyridin-4-yl)boronic acid | HCID 44754822 | — |
| Reactant | 4-((6-bromopyridin-2-yl-amino)methyl)tetrahydro-2H-pyran-4-carbonitrile | HCID 58127276 | — |
| Reactant | ((6-bromopyridin-2-yl-amino)methyl)tetrahydro-2H-pyran-4-carbonitrile | HCID 86689267 | — |
| Catalyst | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| Solvent | 1,2-Dimethoxyethane | HCID 8071 | — |
| Product | 4-(((5'-chloro-2'-fluoro-[2,4'-bipyridin]-6-yl)amino)methyl)tetrahydro-2H-pyran-4-carbonitrile | HCID 58127182 | 75% |
Reaction Steps
A mixture of 4-((6-bromopyridin-2-yl-amino)methyl)tetrahydro-2H-pyran-4-carbonitrile (Intermediate S, 410 mg, 1.384 mmol), 5-chloro-2-fluoropyridin-4-ylboronic acid (362.2 mg, 2.07 mmol), PdCl2(dppf).CH2Cl2 adduct (113 mg, 0.14 mmol), DME (5 Ml) and 2 M aqueous Na2CO2 (1.75 Ml, 3.5 mmol) was sealed and stirred at 110° C. for 20 min using microwave reactor. After cooling to room temperature the mixture was extracted with EtOAc (35 Ml), filtered and concentrated in vacuo. The crude material was purified by column chromatography [silica gel, 24 g, EtOAc/hexane=5/100 to 50/50] to provide 4-((5′-chloro-2′-fluoro-2,4′-bipyridin-6-ylamino)methyl)tetrahydro-2H-pyran-4-carbonitrile (360 mg, 75% yield). LCMS (m/z): 347 [M+H]+; retention time=0.814 min.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08778951B2 |
|---|
| Source dataset | uspto-grants-2014_07 |
|---|
| ORD ID | ord-9032d38ac11c4bd39a288ac3c33aef1a |
|---|
| Source note | uspto-grants-2014_07 |
|---|
