HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1820986Generated: November 1, 2026
N-methyl-2-pyrrolidone → 2-(Morpholin-4-yl)-3-trifluoromethyl-5-cyanopyridine
https://huagongshe.com/reaction/1820986
Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | N-methyl-2-pyrrolidone | HCID 13387 | — |
| Reactant | 4-[5-BRomo-3-(trifluoromethyl)pyridin-2-yl]morpholine | HCID 68852564 | — |
| Catalyst | Zinc cyanide (Zn(CN)2) | HCID 11186 | — |
| Catalyst | Ferrocene-1,1'-bis-(diphenylphosphine) | HCID 635956 | — |
| Catalyst | Bis(dibenzylideneacetone)palladium | HCID 9811564 | — |
| Product | 2-(Morpholin-4-yl)-3-trifluoromethyl-5-cyanopyridine | HCID 68850506 | — |
Reaction Steps
A mixture of 160 mg (0.63 mmol) of 2-(morpholin-4-yl)-3-trifluoromethyl-5-bromopyridine (from Step C), 117 mg (1.0 mmol) of zinc cyanide, 20.1 mg (0.22 mmol) of tris(dibenzylideneacetone)dipalladium(0) and 48.7 mg (0.088) mmol of 1,1′-bis(diphenylphosphino)ferrocene in 2 mL of N-methylpyrrolidinone under argon was stirred at 100° C. for 1 h. The mixture was cooled and partitioned between ether and water. The organic layer was dried and concentrated. Chromatography on a Biotage 40S cartridge using 9:1 v/v hexanes/ether then 17:3 v/v hexanes/ether as the eluant afforded 87 mg of the title compound: ESI-MS (m/z) 258.2; HPLC A: 3.04 min.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US07605171B2 |
|---|
| Source dataset | uspto-grants-2009_10 |
|---|
| ORD ID | ord-e8657ee4ac0048c6ac4882b9e1e8d85c |
|---|
| Source note | uspto-grants-2009_10 |
|---|
