Potassium Phosphate, Tribasic → HCID 86676940, compound

A microwave vial was charged with a mixture of 3,8-dibromo-6-chloroimidazo[1,2-b]pyridazine (1.0 g, 3.21 mmol), 4-methylpyridin-3-ylboronic acid (0.440 g, 3.21 mmol), tetrakis(triphenylphosphine)palladium(0) (0.371 g, 0.321 mmol), dioxane (16 mL), and K3PO4 (4.82 mL, 9.64 mmol) (2.0 M solution in water) was stirred at room temperature for 5 min. under nitrogen. The resulting mixture was heated to 100° C. for 4 h in a microwave heater. The reaction mixture was cooled to room temperature, quenched with water, and diluted with EtOAc. The layers were separated and the aqueous layer was extracted with EtOAc (3×20 mL). The combined organic layers were washed with brine, dried over anhydrous Na2SO4, and filtered. The filtrate was concentrated under reduced pressure. The residue was purified by BIOTAGE® (20-80% EtOAc/CH2Cl2, 1.5 L, then 20%-65% B/CH2Cl2 (0.9 L); B: 10% MeOH/CH2Cl2) to give 320 mg (15.4%) product. 1H NMR (400 MHz, CD3OD) δ ppm 8.91 (1H, s), 8.82 (1H, d, J=5.79 Hz), 8.04 (1H, d, J=5.79 Hz), 7.88 (1H, s), 7.57 (1H, s), 2.54 (3H, s). LC (Conditions B & C): >95% purity; LC/MS: Rt=1.47 min. LC/MS (Condition A): 322.96/324.96.

1. temperatureThe resulting mixture was heated to 100° C. for 4 h in a microwave heater
2. temperatureThe reaction mixture was cooled to room temperature
3. customquenched with water
4. additiondiluted with EtOAc
5. customThe layers were separated
6. extractionthe aqueous layer was extracted with EtOAc (3×20 mL)
7. washThe combined organic layers were washed with brine
8. dry with materialdried over anhydrous Na2SO4
9. filtrationfiltered
10. concentrationThe filtrate was concentrated under reduced pressure
11. customThe residue was purified by BIOTAGE® (20-80% EtOAc/CH2Cl2, 1.5 L

ORD record

ord-cfc3dec3da474bb2b1a9bf751b285d43

Source dataset

uspto-grants-2015_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09145419B2