Potassium Phosphate, Tribasic → (E)-ethyl 3-(5-chloropent-1-enyl)-5-fluoro-1-(3-(naphthalen-1-yloxy)propyl)-1H-indole-2-carboxylate

Participants

Role	Name	HCID	Charge
Reactant	Potassium Phosphate, Tribasic	HCID 62657	—
Reactant	2-[(1E)-5-Chloro-1-penten-1-yl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane	HCID 11128132	—
Reactant	2-Dicyclohexylphosphino-2',6'-dimethoxybiphenyl	HCID 11269872	—
Reactant	ethyl 3-bromo-5-fluoro-1-(3-(naphthalen-1-yloxy)propyl)-1H-indole-2-carboxylate	HCID 67316184	—
Catalyst	palladium(II) acetate	HCID 167845	—
Product	(E)-ethyl 3-(5-chloropent-1-enyl)-5-fluoro-1-(3-(naphthalen-1-yloxy)propyl)-1H-indole-2-carboxylate	HCID 86630290	—

Reaction Conditions

Temperature	100 °C

Reaction Steps

A mixture of ethyl 3-bromo-5-fluoro-1-(3-(naphthalen-1-yloxy)propyl)-1H-indole-2-carboxylate (The synthesis of this compound was described in EXAMPLE 134B as an intermediate) (404 mg), (E)-2-(5-chloropent-1-enyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (0.394 ml), diacetoxypalladium (19.28 mg), dicyclohexyl(2′,6′-dimethoxybiphenyl-2-yl)phosphine (70.5 mg) and K3PO4 (547 mg) was heated in a microwave reactor (CEM Discover) at 100° C. for 1 hour. The insoluble material was removed by filtration and the filtrate was concentrated. The residue was purified by flash chromatography, eluting with dichloromethane to provide the title compound.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08853209B2
Source dataset	uspto-grants-2014_10
ORD ID	ord-7ebb30a835e04004a1aa260f62bb0acc
Source note	uspto-grants-2014_10