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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 59943Generated: October 25, 2026

Triethylamine → Tert-butyl (2-chloro-3-fluoropyridin-4-yl)carbamate

https://huagongshe.com/reaction/59943

Reaction equation

Participants

RoleNameHCIDCharge
ReactantTriethylamineHCID 8471—
ReactantP,P-Diphenylphosphinic azideHCID 199401—
Reactant2-Chloro-3-fluoropyridine-4-carboxylic acidHCID 2782812—
ReactantToluene tert-butyl alcoholHCID 22595558—
SolventWaterHCID 962—
ProductTert-butyl (2-chloro-3-fluoropyridin-4-yl)carbamateHCID 86723306—

Reaction Conditions

Temperature110 °C

Reaction Steps

Diphenylphosphoryl azide (DPPA) (129 mmol) was added to a mixture of 2-chloro-3-fluoro-pyridine-4-carboxylic acid (85.7 mmol), Et3N (257 mmol) in 1:1 tert-BuOH/toluene (200 mL). The mixture was heated at 110° C. for 4 h. Mixture was diluted with H2O and extracted with DCM. The organic layer was dried (Na2SO4) and concentrated. The residue was purified by flash column chromatography (SiO2, 100:0 to 80:20 DCM/EtOAc) to yield the desired product tert-butyl N-(2-chloro-3-fluoro-4-pyridyl)carbamate.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09440929B2
Source datasetuspto-grants-2016_09
ORD IDord-a820ba9736f8407c87728d1a09bd069b
Source noteuspto-grants-2016_09