Potassium Phosphate, Tribasic → methyl 4-(8-cyclopropyl-2-{[6-(1-methyl-1H-pyrazol-4-yl)-4-oxospiro[chroman-2,4'-piperidin]-1'-yl]carbonyl}quinolin-4-yl)benzoate

Participants

Role	Name	HCID	Charge
Reactant	Potassium Phosphate, Tribasic	HCID 62657	—
Reactant	4-Methoxycarbonylphenylboronic acid	HCID 2734369	—
Reactant	8-cyclopropyl-2-{[6-(1-methyl-1H-pyrazol-4-yl)-4-oxospiro[chroman-2,4'-piperidin]-1'-yl]carbonyl}quinolin-4-yl trifluoromethanesulfonate	HCID 58208674	—
Catalyst	Tetrabutylammonium Bromide	HCID 74236	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Solvent	Acetonitrile	HCID 6342	—
Product	methyl 4-(8-cyclopropyl-2-{[6-(1-methyl-1H-pyrazol-4-yl)-4-oxospiro[chroman-2,4'-piperidin]-1'-yl]carbonyl}quinolin-4-yl)benzoate	HCID 58208703	—

Reaction Conditions

Temperature	90 °C

Reaction Steps

K3PO4 (109 mg, 0.515 mmol) was added to a stirred mixture of TBAB (8.30 mg, 0.0260 mmol), PdCl2(dppf) (18.9 mg, 0.0260 mmol), 8-cyclopropyl-2-{[6-(1-methyl-1H-pyrazol-4-yl)-4-oxospiro[chroman-2,4′-piperidin]-1′-yl]carbonyl}quinolin-4-yl trifluoromethanesulfonate (165 mg, 0.258 mmol) and [4-(methoxycarbonyl)phenyl]boronic acid (55.6 mg, 0.309 mmol) in MeCN (2 ml) and the mixture was stirred at 90° C. overnight. The mixture was filtered, washing with CHCl3 and the solvent was evaporated under reduced pressure. The residue was purified by silicagel column chromatography (hexane/EtOAc) to give intended compound as a yellow solid.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08524730B2
Source dataset	uspto-grants-2013_09
ORD ID	ord-db8cf70bebfe4a1e9f524a59f6376d5c
Source note	uspto-grants-2013_09