Acetonitrile → 4-(5-(Trifluoromethyl)pyridin-2-yl)benzaldehyde

Participants

Role	Name	HCID	Charge
Reactant	Acetonitrile	HCID 6342	—
Reactant	Sodium Carbonate	HCID 10340	—
Reactant	4-Formylphenylboronic Acid	HCID 591073	—
Reactant	3-(4-(1-(2-(4-(Trifluoromethyl)phenyl)pyrimidin-5-ylamino)butyl)benzamido)propanoic acid	HCID 67980838	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Product	4-(5-(Trifluoromethyl)pyridin-2-yl)benzaldehyde	HCID 2763359	—

Reaction Steps

To a solution of 4-formylphenylboronic acid (100 g, 0.67 mol) and 2-chloro-5-(trifluoromethyl)pyridine 2 (121 g, 0.67 mol) in acetonitrile (900 mL) was added Pd(dppf)Cl2 (24 g, 33.5 mmol) and 2M aqueous Na2CO3 (837 mL). The resulting mixture was heated at reflux for 3 h under nitrogen atmosphere. The reaction mixture was extracted with ethyl acetate (3*500 mL). The combined organic layers were dried over Na2SO4, filtered and concentrated under reduced pressure. The crude material was purified by silica gel chromatography to give 4-(5-(trifluoromethyl)pyridin-2-yl)benzaldehyde (115 g) as a light yellow solid. 1H NMR (400 MHz CDCl3) δ10.04 (s, 1H), 8.92 (s, 1H), 8.15 (d, J=8.0 Hz, 2H), 7.98 (d, J=8.0 Hz, 1H), 7.96 (d, J=8.0 Hz, 2H), 7.86 (d, J=8.0 Hz, 1H). MS (M+1)=252.0.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08933104B2
Source dataset	uspto-grants-2015_01
ORD ID	ord-fe263ae3d6f54f9d8feac645b7fb5d8d
Source note	uspto-grants-2015_01