Potassium Phosphate, Tribasic → 4-(6-(3,6-dihydro-2H-pyran-4-yl)-3,3-dimethyl-2,3-dihydro-1H-pyrrolo[3,2-b]pyridin-1-yl)-7-fluoro-3-methyl-2-(2-pyridinyl)quinoline

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-(6-bromo-3,3-dimethyl-2,3-dihydro-1H-pyrrolo[3,2-b]pyridin-1-yl)-7-fluoro-3-methyl-2-(pyridin-2-yl)quinoline (150 mg, 0.324 mmol), 2-(3,6-dihydro-2H-pyran-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (102 mg, 0.486 mmol), potassium phosphate tribasic (206 mg, 0.971 mmol), Pd(OAc)2 (72.7 mg, 0.324 mmol) and SPhos (26.6 mg, 0.065 mmol) in toluene (2.5 mL) was heated in the microwave for 1 h at 100° C. After this time the reaction was partitioned between EtOAc (60 mL) and water (30 mL). The separated organic layer was dried over MgSO4, filtered and evaporated in vacuo. Column chromatography (hexanes:EtOAc, 1:0 to 0:1 as eluent) gave 4-(6-(3,6-dihydro-2H-pyran-4-yl)-3,3-dimethyl-2,3-dihydro-1H-pyrrolo[3,2-b]pyridin-1-yl)-7-fluoro-3-methyl-2-(2-pyridinyl)quinoline. 1H NMR (500 MHz, chloroform-d) δ ppm 8.71-8.77 (1H, m), 7.97 (1H, d, J=2.0 Hz), 7.83-7.94 (3H, m), 7.79 (1H, dd, J=9.3, 5.9 Hz), 7.41 (1H, ddd, J=7.3, 4.9, 1.5 Hz), 7.30 (1H, ddd, J=9.2, 8.1, 2.6 Hz), 6.20 (1H, d, J=1.7 Hz), 5.90-5.95 (1H, m), 4.18-4.27 (2H, m), 3.78-3.90 (4H, m), 2.29-2.44 (5H, m), 1.61 (3H, s), 1.55 (3H, s). Mass Spectrum (ESI) m/e=467.2 (M+1).

Provenance & Evidence