Potassium Fluoride → tert-butyl N-[4-(3-cyano-1-cyclobutyl-6-cyclopropyl-indol-2-yl)phenyl]carbamate

Participants

Role	Name	HCID	Charge
Reactant	Potassium Fluoride	HCID 522689	—
Reactant	Cyclopropylboronic acid	HCID 2760897	—
Reactant	[4-(6-bromo-3-cyano-1-cyclobutyl-1H-indol-2-yl)-phenyl]-carbamic acid tert-butyl ester	HCID 59430631	—
Catalyst	Palladium, tris[mu-[(1,2-eta:4,5-eta)-(1E,4E)-1,5-diphenyl-1,4-pentadien-3-one]]di-, compd. with trichloromethane (1:1)	HCID 11029508	—
Solvent	Tetrahydrofuran	HCID 8028	—
Product	tert-butyl N-[4-(3-cyano-1-cyclobutyl-6-cyclopropyl-indol-2-yl)phenyl]carbamate	HCID 49773195	59%

Reaction Conditions

Temperature	60 °C

Reaction Steps

A mixture of [4-(6-bromo-3-cyano-1-cyclobutyl-1H-indol-2-yl)-phenyl]-carbamic acid tert-butyl ester (0.17 g, 0.4 mmol), cyclopropylboronic acid (0.047 g, 0.55 mmol), (tert-butyl)3PHBF4 (0.014 g, 0.048 mmol), KF (0.093 g, 1.6 mmol), and Pd2(dba)3-CHCl3, 0.021 g, 0.02 mmol) in THF (2.0 mL) was stirred at 60° C. overnight. The mixture was concentrated, taken up in CH2Cl2 and filtered through Celite. The solid was washed with CH2Cl2 and the filtrate was purified on silica gel (CH2Cl2) to provide [4-(3-cyano-1-cyclobutyl-6-cyclopropyl-1H-indol-2-yl)-phenyl]-carbamic acid tert-butyl ester as a solid (0.10 g, 59%).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07973069B2
Source dataset	uspto-grants-2011_07
ORD ID	ord-5b01492a76df4a3185997435a50fefa9
Source note	uspto-grants-2011_07