Tetrahydrofuran → 2-Cyclopropyl-4-methylpyridin-3-amine

Participants

Reaction Conditions

Reaction Steps

Following a modified synthetic procedure reported in J. Org. Chem. 2003, 68, 5534, a mixture of 2-bromo-4-methylpyridin-3-amine (1.0 eq.), potassium cyclopropyltrifluoroborate (2.0 eq.), Cs2CO3 (3.0 eq.) and PdCl2(dppf)-CH2Cl2 adduct (0.1 eq.) in 10:1 solution THF:H2O (0.14M) 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 heated for O/N at 80° C. After completion of the reaction, the vial was cooled to RT 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 10-100% EtOAc/petroleum ether affording the titled compound as brown oil. 1H-NMR (400 MHz, DMSO-d6, 300K) δ 7.55 (1H, d, J=4.7 Hz), 6.75 (1H, d, J=4.7 Hz), 4.89 (2H, br. s), 2.13-2.04 (4H, m), 0.85-0.68 (4H, m). MS (ES) C9H12N2 requires: 148, found: 149 (M+H)+.

Provenance & Evidence