Sodium Carbonate → 4-(4-Formylpyridin-3-yl)-2-methylbenzonitrile

Participants

Role	Name	HCID	Charge
Reactant	Sodium Carbonate	HCID 10340	—
Reactant	3-Bromopyridine-4-carboxaldehyde	HCID 2762997	—
Reactant	2-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile	HCID 45158520	—
Catalyst	HCID 178418476	HCID 178418476	—
Solvent	Dimethylformamide	HCID 6228	—
Product	4-(4-Formylpyridin-3-yl)-2-methylbenzonitrile	HCID 86674833	78.4%

Reaction Conditions

Temperature	100 °C

Reaction Steps

A mixture of 1a (430 mg, 1.769 mmol), 3-bromo-4-pyridinecarboxaldehyde (299 mg, 1.608 mmol), sodium carbonate (2N in water, 1.608 mL, 3.22 mmol), bis(triphenylphosphine)palladium(II) chloride (28.2 mg, 0.040 mmol) in DMF (6.432 mL) was heated to 100° C. for 2 hrs. The mixture was quenched with saturated NaHCO3 and extracted with EtOAc two times, dried over magnesium sulfate, filtered and concentrated. The residue was purified via Biotage (0-50% EtOAc/heptane; 25M column) giving compound 1b as white solid (280 mg, 78%). LC-MS (M+1) 223.1, t=1.28 min.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08519134B2
Source dataset	uspto-grants-2013_08
ORD ID	ord-6ebd6bad38714eeb8ecf4ce25d5ab0e2
Source note	uspto-grants-2013_08