Cesium fluoride → 4-(2-Fluoro-5-methylsulfonylphenyl)-2-methylisoquinolin-1-one

Participants

Role	Name	HCID	Charge
Reactant	Cesium fluoride	HCID 25953	—
Reactant	2-Bromo-1-fluoro-4-(methylsulfonyl)benzene	HCID 67387081	—
Reactant	2-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)isoquinolin-1(2H)-one	HCID 123809499	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Solvent	Methanol	HCID 887	—
Solvent	1,2-Dimethoxyethane	HCID 8071	—
Product	4-(2-Fluoro-5-methylsulfonylphenyl)-2-methylisoquinolin-1-one	HCID 118021901	74.4%

Reaction Conditions

Temperature	70 °C

Reaction Steps

A mixture of compound 2-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)isoquinolin-1-one (4.1 g, 14.5 mmol), 2-bromo-4-methylsulfonyl-1-fluorobenzene (3.5 g, 13.8 mmol) prepared in a similar manner to Example 79 steps 1-2, CsF (6.3 g, 41.3 mmol), and Pd(dppf)Cl2 (1.0 g, 1.38 mmol) in DME (70 mL) and MeOH (35 ml) was stirred at 70° C. for 12 h under N2. The mixture was concentrated and the residue was purified by column chromatography on silica gel (PE:EA=2:1-0:1) to give the title compound (3.4 g, 74.4%) as a red solid. LCMS (M+H)+=331.9 (M+1)+

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09034900B2
Source dataset	uspto-grants-2015_05
ORD ID	ord-5e73275848534ed28973ef408d5e6d1d
Source note	uspto-grants-2015_05