Diisopropylethylamine → 6-((11-Hydroxyundecyl)thio)-4-((3-methoxyphenyl)amino)-8-methylquinoline-3-carboxamide

https://huagongshe.com/reaction/1944885

Participants

Role	Name	HCID	Charge
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	11-Mercaptoundecanol	HCID 261824	—
Reactant	1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)	HCID 636044	—
Reactant	6-Iodo-4-(3-methoxyphenylamino)-8-methylquinoline-3-carboxamide	HCID 57516947	—
Catalyst	Bis(dibenzylideneacetone)palladium	HCID 9811564	—
Solvent	1,4-Dioxane	HCID 31275	—
Product	6-((11-Hydroxyundecyl)thio)-4-((3-methoxyphenyl)amino)-8-methylquinoline-3-carboxamide	HCID 58505144	—

Reaction Steps

The title compound was synthesized in a manner analogous to that described in Org. Lett. 2004, 6(24), 4587-4590. To a round bottom flask were added 6-iodo-4-((3-methoxyphenyl)amino)-8-methylquinoline-3-carboxamide (1.0 g, 2.31 mmol), dry dioxane (23 mL) and i-Pr2NEt (0.81 mL, 4.62 mmol). Catalytic Pd2(dba)3 (63 mg, 0.07 mmol), Xantphos (80 mg, 0.14 mmol) and 11-mercapto-1-undecanol (494 mg, 2.42 mmol) were then added. The mixture was evacuated and backfilled with nitrogen (3 cycles). The mixture was heated to reflux for 2 h (HPLC confirmed the completion of the reaction). The reaction mixture was then allowed to reach ambient temperature followed by filtration and concentration. The crude product was used without further purification for the next step. ES/MS calcd. for C29H40N3O3S+ 510.3. Found m/z=510.4 (M+H)+.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08394829B2
Source dataset	uspto-grants-2013_03
ORD ID	ord-7c49e4b130e34235918db9a4dc0d39cc
Source note	uspto-grants-2013_03