Acetone → HCID 67155071, compound

Participants

Reaction Conditions

Reaction Steps

n-BuLi 1.6M in hexanes (11.25 ml, 18.00 mmol) was added dropwise to a solution of diisopropylamine (2.78 ml, 19.50 mmol) in THF (50.0 ml) at −78° C. under N2. The resulting mixture was warmed up to −40° C. and stirred for 10 min and recooled to −78° C. 3-bromo-5-fluoropyridine (2.64 g, 15 mmol) in 5 mL THF was added dropwise at this temperature. After 30 min, acetone (3.30 ml, 45.0 mmol) was added dropwise and the resulting mixture was stirred for 30 min at −78° C., and then for another 30 min at 0° C. The mixture was quenched with saturated NH4Cl and extracted with EtOAc two times, dried over magnesium sulfate, filtered, concentrated. The residue was purified via Biotage (0-30% AcOEt/heptane, SNAP50) giving 10a (1.691 g, 48%) as a yellow oil. LC-MS (M+1) 235.9, t=1.18 min.

Provenance & Evidence