proline dl-form → HCID 54445738, compound

Participants

Role	Name	HCID	Charge
Reactant	proline dl-form	HCID 614	—
Reactant	Triethylamine	HCID 8471	—
Reactant	Potassium Carbonate	HCID 11430	—
Reactant	Triethylamine hydrobromide	HCID 12493	—
Reactant	1,4-Dibromo-2-fluorobenzene	HCID 137004	—
Reactant	K2CO3 Et2O	HCID 86755020	—
Catalyst	Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)	HCID 24350	—
Catalyst	HCID 178418397	HCID 178418397	—
Solvent	N,N-Dimethylformamide--water (1/1)	HCID 21962138	—
Product	HCID 54445738	HCID 54445738	—

Reaction Conditions

Temperature	120 °C

Reaction Steps

To a solution of DL-proline (576 mg, 5 mmol) in 10/1 DMF-H2O (7.5 ml) at RT were added CuI (48 mg, 0.25 mmol), Pd(PPh3)4 (290 mg, 0.25 mmol), K2CO3 (690 mg, 5 mmol), NEt3 (1.4 ml, 10 mmol), triethylammonium bromide (158 mg, 0.75 mmol), and 1,4-dibromo-2-fluorobenzene. The resulting mixture was stirred in a sealed tube at 120° C. for 48 hours. The reaction mixture was cooled to room temperature and poured onto saturated K2CO3 /Et2O. The aqueous layer was extracted 3× with Et2O. The pH of the aqueous layer was adjusted to 4 and extracted 3× with EtOAc. The combined organics were washed with brine, dried over MgSO4, and concentrated in vacuo to produce title compound which was used without further purification: LCMS (M+1)=287. ##STR393##

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US06011059
Source dataset	uspto-grants-2000_01
ORD ID	ord-8ddff6181fa046e180dda31bb25f3ba9
Source note	uspto-grants-2000_01