Ethyl Acetate → 1-(2,6-Dimethylpyrimidin-4-yl)-4-fluoro-1-(3-(pyrimidin-5-yl)phenyl)-1H-isoindol-3-amine

Participants

Role	Name	HCID	Charge
Reactant	Ethyl Acetate	HCID 8857	—
Reactant	Cesium carbonate	HCID 10796	—
Reactant	(Pyrimidin-5-yl)boronic acid	HCID 2795193	—
Reactant	1-(3-Bromophenyl)-1-(2,6-dimethylpyrimidin-4-yl)-4-fluoro-1H-isoindol-3-amine	HCID 58579526	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Solvent	Water	HCID 962	—
Solvent	Sodium chloride; water	HCID 57417360	—
Solvent	Dimethoxyethane ethanol water	HCID 86587095	—
Product	1-(2,6-Dimethylpyrimidin-4-yl)-4-fluoro-1-(3-(pyrimidin-5-yl)phenyl)-1H-isoindol-3-amine	HCID 46202744	16.4%

Reaction Conditions

Temperature	150 °C

Reaction Steps

1-(3-Bromophenyl)-1-(2,6-dimethylpyrimidin-4-yl)-4-fluoro-1H-isoindol-3-amine (300 mg, 0.73 mmol), pyrimidin-5-ylboronic acid (108 mg, 0.88 mmol), cesium carbonate (713 mg, 2.19 mmol) and dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium (II) dichloromethane adduct (59.6 mg, 0.07 mmol) were dissolved in DME:EtOH:water (6:3:1) (5 mL) and heated in a microwave oven for 20 min at 150° C. EtOAc, water and brine were added and the organic phase was collected, dried and filtered. The solvent was removed under reduced pressure and the residue was purified by preparative HPLC to afford 49 mg (15%) of the title compound.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08030500B2
Source dataset	uspto-grants-2011_10
ORD ID	ord-e5bd699261474cb4a7f9849b632f83e1
Source note	uspto-grants-2011_10