Dimethylformamide → 4-Fluoro-1-(2-fluoro-5-(pyrimidin-5-yl)phenyl)-1-(2-methylpyridin-4-yl)-1H-isoindol-3-amine

Participants

Role	Name	HCID	Charge
Reactant	Dimethylformamide	HCID 6228	—
Reactant	Potassium Carbonate	HCID 11430	—
Reactant	(Pyrimidin-5-yl)boronic acid	HCID 2795193	—
Reactant	1-(5-Bromo-2-fluorophenyl)-4-fluoro-1-(2-methylpyridin-4-yl)-1H-isoindol-3-amine	HCID 58579499	—
Catalyst	HCID 178477754	HCID 178477754	—
Solvent	Sodium chloride; water	HCID 57417360	—
Product	4-Fluoro-1-(2-fluoro-5-(pyrimidin-5-yl)phenyl)-1-(2-methylpyridin-4-yl)-1H-isoindol-3-amine	HCID 46205637	43.3%

Reaction Conditions

Temperature	150 °C

Reaction Steps

1-(5-Bromo-2-fluorophenyl)-4-fluoro-1-(2-methylpyridin-4-yl)-1H-isoindol-3-amine (80 mg, 0.19 mmol), 5-pyrimidinylboronic acid (31.1 mg, 0.25 mmol), [1,1-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (15.77 mg, 0.02 mmol), potassium carbonate (2.5 M, aq, 0.290 mL, 0.58 mmol) and DMF (2 mL) were added to a vial and heated in a microwave reactor at 150° C. for 15 min. Brine was added and the product mixture was extracted EtOAc. The organic phase was dried (Na2SO4), filtered and concentrated in vacuo. Purification by preparative HPLC afforded 34.0 mg (43% yield) 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-b57761e9d39146669859980376aeba9b
Source note	uspto-grants-2011_10