Sodium Carbonate → 4-(3-Methoxyphenyl)-2-methylisoquinolin-1-one

Participants

Role	Name	HCID	Charge
Reactant	Sodium Carbonate	HCID 10340	—
Reactant	Triphenylphosphine	HCID 11776	—
Reactant	4-Bromo-2-methylisoquinolin-1(2H)-one	HCID 311858	—
Reactant	(3-Methoxyphenyl)boronic acid	HCID 2734370	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Solvent	Water	HCID 962	—
Solvent	Ethyl Acetate	HCID 8857	—
Solvent	1,4-Dioxane	HCID 31275	—
Product	4-(3-Methoxyphenyl)-2-methylisoquinolin-1-one	HCID 118021804	17%

Reaction Conditions

Temperature	90 °C

Reaction Steps

A mixture of 4-bromo-2-methylisoquinolin-1(2H)-one (100 mg, 0.42 mmol), and (3-methoxyphenyl)boronic acid (70 mg, 0.46 mmol), PPh3 (66 mg, 0.25 mmol), Na2CO3 (133 mg, 1.26 mmol), and Pd(dppf)Cl2 (62 mg, 0.084 mmol) in dioxane (2.5 mL) and water (0.5 mL) was heated overnight at 90° C. Extractive work up with ethyl acetate followed by preparative TLC (PE:EA=1:1) gave the title compound (18 mg, 0.07 mmol) as a white solid in 17% yield. 1H NMR (DMSO, 400 MHz): δ 8.30 (d, 1H, J=7.68), 7.68 (t, 1H, J=7.56), 7.50-7.55 (m, 3H), 7.40 (t, 1H, J=7.44), 6.97-7.00 (m, 3H), 3.78 (s, 3H), 3.54 (s, 3H). MS (m/z, relative intensity): 266 (M+, 1).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09034900B2
Source dataset	uspto-grants-2015_05
ORD ID	ord-b3f66d201728468dbf6bcfc4732ffac3
Source note	uspto-grants-2015_05