Tetrahydrofuran → HCID 67231943, compound

Participants

Reaction Conditions

Reaction Steps

Following a modified synthetic procedure reported in J. Org. Chem. 2003, 68, 5534 a mixture of 2-bromo-4-chloropyridin-3-amine (prepared as described in US2002/0119982) (1.0 eq.), cyclopropylboronic acid (2.0 eq.), Cs2CO3 (3.0 eq.) and PdCl2(dppf)-CH2Cl2 adduct (0.1 eq.) in 10:1 solution THF:H2O (0.14 M) was put in a 10-mL glass vial equipped with a small magnetic stirring bar. The reaction vessel was fitted with a rubber septum, was evacuated and back-filled with argon and sealed with an aluminum/Teflon crimp top. The reaction mixture was then irradiated for 1 h at 120° C., using an irradiation power of 100 W. After completion of the reaction, the vial was cooled to 50° C. with air jet cooling before it was opened. The reaction mixture was diluted with EtOAc and filtered on a pad of Solca Floc®200FCC. The crude product was purified by flash chromatography eluting with 5-100% EtOAc/petroleum ether affording the titled compound as yellow oil. 1H-NMR (400 MHz, DMSO-d6, 300K) δ 7.59 (1H, d, J=5.1 Hz), 7.04 (1H, d, J=5.1 Hz), 5.42 (2H, br. s), 2.24-2.15 (1H, m), 0.92-0.82 (4H, m). MS (ES) C8H9ClN2 requires: 168, found: 169, 171 (M+H)+.

Provenance & Evidence