Dichloromethane → HCID 57834996, compound

Participants

Role	Name	HCID	Charge
Reactant	Dichloromethane	HCID 6344	—
Reactant	Potassium Carbonate	HCID 11430	—
Reactant	Tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,6-tetrahydropyridine-1-carboxylate	HCID 4642098	—
Reactant	4-Bromo-1-[(3-fluorophenyl)methyl]-1H-indole-2,3-dione	HCID 28492477	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Solvent	1,4-Dioxane	HCID 31275	—
Product	HCID 57834996	HCID 57834996	—

Reaction Conditions

Temperature	80 °C

Reaction Steps

4-Bromo-1-(3-fluoro-benzyl)-1H-indole-2,3-dione (167 mg) was dissolved in 2.5 mL of dioxane and 4-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester (154 mg) was added, followed by [1,1′-bis(diphenylphosphino)-ferrocene]dichloropalladium(II), complex with dichloromethane (1:1) (24 mg) and K2CO3 (138 mg). The reaction mixture was heated to 80° C. for 18 hours and then cooled and concentrated under reduced pressure. The resulting residue was purified by chromatography to afford 4-[1-(3-Fluoro-benzyl)-2,3-dioxo-2,3-dihydro-1H-indol-4-yl]-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester. MS: 337 (M−Boc+H)+.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07582760B2
Source dataset	uspto-grants-2009_09
ORD ID	ord-dbab6cdef5a94718a4a034fd2f53196c
Source note	uspto-grants-2009_09