Potassium Carbonate → 1186234-39-8

Temperature

100 °C

A solution of 4-fluorophenyl boronic acid (0.254 mg, 1.81 mmol) in THF/H2O (10:1; 10 mL) was added to a microwave vial containing 3-(5-iodo-pyridin-2-yloxy)-azetidine-1-carboxylic acid pyridazin-3-ylamide (Example 7, Step 1) (0.480 g, 1.21 mmol) and potassium carbonate (0.50 g, 3.63 mmol). Nitrogen gas was bubbled through the mixture for 5 mins then 1,1′-bis[(diphenylphosphino)-ferrocene]dichloropalladium(II) complex with CH2Cl2 (0.099 g, 10 mole %) was added and the vial sealed and heated at 100° C. in microwave synthesiser for 30 min. The cooled reaction mixture was diluted with ethyl acetate (20 mL) and washed sequentially with saturated aqueous sodium carbonate solution (20 mL) then saturated sodium chloride solution (20 mL). The mixture was dried over magnesium sulphate and filtered. Filtrate solvents were removed in vacuo to afford a brown gum, which was purified by flash chromatography, eluting with a gradient of 50% to 100% ethyl acetate in hexane to a afford a white solid (0.235 g, 53%)

1. customNitrogen gas was bubbled through the mixture for 5 mins
2. addition1,1′-bis[(diphenylphosphino)-ferrocene]dichloropalladium(II) complex with CH2Cl2 (0.099 g, 10 mole %) was added
3. customthe vial sealed
4. customThe cooled reaction mixture
5. washwashed sequentially with saturated aqueous sodium carbonate solution (20 mL)
6. dry with materialThe mixture was dried over magnesium sulphate
7. filtrationfiltered
8. customFiltrate solvents were removed in vacuo
9. customto afford a brown gum, which
10. customwas purified by flash chromatography
11. washeluting with a gradient of 50% to 100% ethyl acetate in hexane to

ORD record

ord-6ff43132d5194623a40b5c8002cdcf66

Source dataset

uspto-grants-2015_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09006269B2