Lithium diisopropylamide → HCID 57425783, compound

Participants

Reaction Steps

To a solution of di-3-pyridylmethane (250 mg, 1.47 mmol) in dry TIE (5 mL) was added LDA (2.1 mL, 3.16 mmol) slowly at −78° C. After 30 min a solution of methyl 2-bromopyridine-6-carboxylate (349 mg, 1.62 mmol) in dry THF (3 mL) was added slowly. After 30 min the cooling bath was removed and the mixture allowed to warm to RT. After 4 hr the mixture was diluted with saturated NH4Cl and extracted with EtOAc (3×). The combined organic layers were dried (MgSO4), filtered, and concentrated. Flash column (100% EtOAc) gave 1-(6-bromopyridin-2-yl)-2,2-dipyridin-3-ylethanone as a yellow oil. 1H-NMR (500 MHz, CDCl3) δ 8.66 (m, 2 H), 8.53 (m, 2 H), 8.06 (dd, J=0.98 and 6.35 Hz, 1 H), 7.80 (m, 4 H), 7.28 (m, 2 H), 6.79 (s, 1 H).

Provenance & Evidence