Ammonium Chloride → HCID 71008574, compound

Participants

Reaction Conditions

Reaction Steps

5-(1-(azetidin-1-yl)-2-methylpropan-2-yloxy)-2-chloropyridine (3.5 g, 14.5 mmol, Eq: 1.00) was dissolved in tetrahydrofuran (78.0 ml). 2-(Dicyclohexylphosphino)biphenyl (1.02 g, 2.91 mmol, Eq: 0.2), then tris(dibenzylideneacetone)dipalladium(0) (1.33 g, 1.45 mmol, Eq: 0.1) were added under an argon atmosphere. Finally 1M lithium bis(trimethylsilyl)amide in THF (43.6 ml, 43.6 mmol, Eq: 3) was added dropwise. The reaction mixture was stirred under argon atmosphere at 75° C. over night. The reaction mixture was poured into 100 ml saturated NH4Cl and extracted with EtOAc (100 ml). The organic phase and washed with 50% diluted brine. The aqueous phase was back extracted with 2×80 ml EtOAc. The combined organic phase was dried (MgSO4), filtered and concentrated in vacuo. The crude material was purified by Analogix MPLC (40 g column (eluted with 1% to 10% MeOH in DCM) to afford the desired product (1.66 g) as a brown viscous oil. 1H NMR (300 MHz, CHLOROFORM-d) δ ppm 1.18 (s, 6 H) 2.10 (quin, J=7.08 Hz, 2 H) 2.54 (s, 2 H) 3.33 (t, J=6.99 Hz, 4 H) 4.25 (br. s., 2 H) 6.43 (d, J=8.69 Hz, 1 H) 7.12 (dd, J=8.69, 2.64 Hz, 1 H) 7.79 (d, J=2.64 Hz, 1 H).

Provenance & Evidence