Potassium Hydroxide → HCID 59627924, compound

Participants

Role	Name	HCID	Charge
Reactant	Potassium Hydroxide	HCID 14797	—
Reactant	Phosphine	HCID 24404	—
Reactant	Di-tert-butyl(2',4',6'-tris(propan-2-yl)-(1,1'-biphenyl)-2-yl)phosphane	HCID 11618717	—
Reactant	4-bromo-6-fluoro-1-{4-[(phenylmethyl)oxy]phenyl}-1H-indole	HCID 59627933	—
Catalyst	Bis(dibenzylideneacetone)palladium	HCID 9811564	—
Solvent	Water	HCID 962	—
Solvent	Dichloromethane	HCID 6344	—
Solvent	1,4-Dioxane	HCID 31275	—
Product	HCID 59627924	HCID 59627924	44.6%

Reaction Conditions

Temperature	85 °C

Reaction Steps

A mixture of 4-bromo-6-fluoro-1-{4-[(phenylmethyl)oxy]phenyl}-1H-indole (D19) (200 mg, 0.505 mmol) and potassium hydroxide (113 mg, 2.02 mmol) in 1,4-dioxan (3 mL)/water (3 mL) was treated with Pd2dba3 (9 mg, 0.02 mmol) and phosphine ligand, bis(1,1-dimethylethyl)[2′,4′,6′-tris(1-methylethyl)-2-biphenylyl]phosphane (11 mg, 0.05 mmol) and the mixture was heated to 85° C. for 1.5 hours. After cooling, the mixture was diluted with dichloromethane and water and the product was extracted into dichloromethane. The combined organic layers were dried (MgSO4) and evaporated. Chromatography on silica gel (elution with 0-50% ethyl acetate in hexane) gave the title compound (D20), (75 mg).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07956083B2
Source dataset	uspto-grants-2011_06
ORD ID	ord-015c562cae714ff8a34db46a2809a9c4
Source note	uspto-grants-2011_06