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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1962432Generated: October 31, 2026

Potassium Phosphate, Tribasic → (S)-3-(tert-Butoxycarbonylamino)-1-(4-cyclopropyl-5-isoquinolinesulfonyl)pyrrolidine

https://huagongshe.com/reaction/1962432

Reaction equation

Participants

RoleNameHCIDCharge
ReactantPotassium Phosphate, TribasicHCID 62657—
ReactantCyclopropylboronic acidHCID 2760897—
ReactantTricyclohexylphosphonium TetrafluoroborateHCID 11710396—
Reactant(S)-3-(tert-Butoxycarbonylamino)-1-(4-bromo-5-isoquinolinesulfonyl)pyrrolidineHCID 67242852—
Catalystpalladium(II) acetateHCID 167845—
SolventTolueneHCID 1140—
SolventEthyl AcetateHCID 8857—
Product(S)-3-(tert-Butoxycarbonylamino)-1-(4-cyclopropyl-5-isoquinolinesulfonyl)pyrrolidineHCID 6724319629%

Reaction Conditions

Temperature80 °C

Reaction Steps

A suspension of Intermediate 1a (200 mg) obtained in Example 1-1, Step A, cyclopropylboronic acid (57 mg, Aldrich), anhydrous potassium phosphate (372 mg, Aldrich), and tricyclohexylphosphonium tetrafluoroborate (33 mg, Aldrich) in toluene (2 ml) was added with palladium acetate (10 mg, Wako Pure Chemical Industries), and the mixture was stirred at 80° C. with heating for 14 hours under a nitrogen gas atmosphere. The reaction mixture was cooled to room temperature, and then added with ethyl acetate (5 ml), and the insoluble solids were removed by filtration through Celite. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel chromatography (n-hexane:ethyl acetate=1:1) to obtain the title compound (53 mg).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08415372B2
Source datasetuspto-grants-2013_04
ORD IDord-d67768e3bd00415a97a2653785651add
Source noteuspto-grants-2013_04