2-Bromopyridine → 2-Methyl-6-pyridin-2-ylisoquinolin-1-one

Participants

Role	Name	HCID	Charge
Reactant	2-Bromopyridine	HCID 7973	—
Reactant	Sodium Bicarbonate	HCID 516892	—
Reactant	2-Methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2-dihydroisoquinolin-1-one	HCID 121228834	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Solvent	Dimethyl Sulfoxide	HCID 679	—
Product	2-Methyl-6-pyridin-2-ylisoquinolin-1-one	HCID 118022208	46.1%

Reaction Steps

A mixture of 2-methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)isoquinolin-1-one (420 mg, 1.47 mmol), 2-bromopyridine (698 mg, 4.42 mmol), Pd(dppf)Cl2 (107 mg, 0.15 mmol) and saturated aqueous NaHCO3 (3.5 mL) in DMSO (25 mL) was microwaved at 150° C. for 45 min. After extractive work up with ethyl acetate, purification by silica gel chromatography (PE:EA=3:1 to 3:2) gave the title compound (160 mg, 46.0%) as a white solid. 1H NMR (CDCl3, 400 MHz) δ 8.76 (d, J=4.8 Hz, 1H), 8.53 (d, J=8.0 Hz, 1H), 8.20 (d, J=1.2 Hz, 1H), 8.07 (dd, J1=8.4 Hz, J2=1.6 Hz, 1H), 7.85-7.82 (m, 2H), 7.34-7.30 (m, 1H), 7.11 (d, J=7.2 Hz, 1H), 6.6 (d, J=7.2 Hz, 1H), 3.64 (s, 3H). LCMS: 237.2 (M+H)+

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09034900B2
Source dataset	uspto-grants-2015_05
ORD ID	ord-b23bd43242464c37a474338ce9807287
Source note	uspto-grants-2015_05