Cesium carbonate → HCID 59706185, compound

Participants

Reaction Conditions

Reaction Steps

The 2-bromo-6-[1-(3,3-difluoropyrrolidin-1-yl)-2,2-dipyridin-3-ylethyl]pyridine (73 mg, 0.16 mmol), tert-butyl carbamate (23 mg, 0.2 mmol), Cs2CO3 (75 mg, 0.23 mmol), Pd2(dba)3 (3 mg, 0.003 mmol), and xantphos (6 mg, 0.01 mmol) were combined in dry 1,4-dioxane (1.5 mL). The mixture was degassed (3× pump/N2) then heated to 100° C. After 5 hr the mixture was cooled to RT, diluted with EtOAc, filtered through a pad of Celite, and concentrated. The residue was taken up in 1 mL CH2Cl2 to which was added 1 mL TFA at RT. After 90 min the mixture was concentrated. The residue was taken up in saturated NaHCO3 and extracted with CH2Cl2 (3×). The combined organic layers were dried (MgSO4), filtered, and concentrated. Flash column (gradient, 0-10% MeOH/CH2Cl2) gave the title compound as a yellow foam. 1H-NMR (500 MHz, CDCl3) δ 8.68 (d, J=2.20 Hz, 1 H), 8.47 (d, J=4.15 Hz, 1 H), 8.37 (d, J=2.19 Hz, 1 H), 8.25 (d, J=3.90 Hz, 1 H), 7.74 (d, J=8.06 Hz, 1 H), 7.41 (d, J=7.81 Hz, 1 H), 7.25 (m, 2 H), 7.02 (m 1 H), 6.27 (m, 2 H), 4.85 (d, J=11.47 Hz, 1 H), 4.39 (s, 2 H), 4.35 (d, J=11.72 Hz, 1 H), 3.10 (m, 1 H), 2.86 (m, 2 H), 2.67 (m, 1 H), 2.0 (m, 2 H); MS (M+H)+ 382.0.

Provenance & Evidence