Dichloromethane → methyl 4-(2-(pyridin-2-yl)-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl)quinoline-6-carboxylate

Participants

Role	Name	HCID	Charge
Reactant	Dichloromethane	HCID 6344	—
Reactant	Sodium Acetate	HCID 517045	—
Reactant	6-bromo-4-(2-(pyridin-2-yl)-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl)quinoline	HCID 10135027	—
Reactant	HCID 178418416	HCID 178418416	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Solvent	Methanol	HCID 887	—
Product	methyl 4-(2-(pyridin-2-yl)-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl)quinoline-6-carboxylate	HCID 10133736	—

Reaction Steps

To a mixture of sodium acetate (0.84 g, 10.2 mmol) and [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium (II):CH2Cl2 (42 mg, 0.05 mmol) in methanol (40 mL) is added 6-bromo-4-(2-pyridin-2-yl-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl)-quinoline (1.0 g, 2.56 mmol). The mixture is heated at 90° C. under 68 psi carbon monoxide for 24 h. The mixture is cooled, filtered, and concentrated in vacuo. The product is partitioned between ethyl acetate and: water. The organic layer is dried over sodium sulfate and concentrated in vacuo. The residue is chromatographed on SiO2 (dichloromethane to 2% methanol/dichloromethane) to yield a solid, 918 mg (97%).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07087626B2
Source dataset	uspto-grants-2006_08
ORD ID	ord-8a78da593f264a14928d76c76ca79538
Source note	uspto-grants-2006_08