Back
HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1510558Generated: October 27, 2026

Triphenylphosphine → 3-{5-[4-(4-Bromo-2-fluorophenylamino)-1,5-dimethyl-6-oxo-1,6-dihydro-pyridin-3-yl]-tetrazol-1-yl}-propionitrile

https://huagongshe.com/reaction/1510558

Reaction equation

Participants

RoleNameHCIDCharge
ReactantTriphenylphosphineHCID 11776—
ReactantAzidotrimethylsilaneHCID 78378—
ReactantDiisopropyl azodicarboxylateHCID 5363146—
Reactant4-(4-Bromo-2-fluorophenylamino)-1,5-dimethyl-6-oxo-1,6-dihydropyridine-3-carboxylic acid (2-cyano-ethyl)-amideHCID 66674377—
SolventAcetonitrileHCID 6342—
SolventEthyl AcetateHCID 8857—
Product3-{5-[4-(4-Bromo-2-fluorophenylamino)-1,5-dimethyl-6-oxo-1,6-dihydro-pyridin-3-yl]-tetrazol-1-yl}-propionitrileHCID 6667443461%

Reaction Steps

PPh3 (83 mg, 0.32 mmol) was added to a stirred suspension of 4-(4-bromo-2-fluorophenylamino)-1,5-dimethyl-6-oxo-1,6-dihydropyridine-3-carboxylic acid (2-cyano-ethyl)-amide (51 mg, 0.12 mmol) in MeCN (1.5 mL). DIAD (0.065 mL, 0.31 mmol) and TMSN3 (0.045 mL, 0.32) were added dropwise. After 22 hours, the reaction mixture was diluted with ethyl acetate and washed with water. The aqueous layer was extracted with ethyl acetate. The combined organic extracts were dried (MgSO4) and concentrated under reduced pressure. Purification by flash column chromatography gave clean desired product (33 mg, 61%).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08211921B2
Source datasetuspto-grants-2012_07
ORD IDord-d3df444ce2624b239f68c7df8a966904
Source noteuspto-grants-2012_07