Dichloromethane → N-(4-tert-butylphenyl)-4-(3-isoxazolyl)benzamide

Participants

Role	Name	HCID	Charge
Reactant	Dichloromethane	HCID 6344	—
Reactant	Tetrahydrofuran	HCID 8028	—
Reactant	Triethylamine	HCID 8471	—
Reactant	4-Tert-Butylaniline	HCID 69861	—
Reactant	3-(4-Bromophenyl)isoxazole	HCID 12647752	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Product	N-(4-tert-butylphenyl)-4-(3-isoxazolyl)benzamide	HCID 11186273	—

Reaction Conditions

Temperature	120 °C

Reaction Steps

The product from Example 42C (56.1 mg, 0.250 mmol), triethylamine (55 μL, 0.39 mmol), 4-tert-butylaniline (52 μL, 0.33 mmol), and Pd(dppf)Cl2:CH2Cl2 (20.4 mg, 0.025 mmol) were combined in tetrahydrofuran (10 mL) and heated at 120° C. under a carbon monoxide atmosphere (700 psi) for 16 hours. The mixture was allowed to cool to room temperature and concentrated under reduced pressure. The residue was purified by flash chromatography (20% ethyl acetate in hexanes) to provide the title compound as a solid. 1H NMR (300 MHz, CDCl3)δ 8.51 (d, 1H), 7.96 (s, 4H), 7.82 (br s, 1H), 7.57 (d, 2H), 7.41 (d, 2H), 6.73 (d, 1H), 1.33 (s, 9H); MS (m/z) 321.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07037927B2
Source dataset	uspto-grants-2006_05
ORD ID	ord-a5b25b4b231b4921a3a6f7bb1d50f37a
Source note	uspto-grants-2006_05