Sodium Carbonate → HCID 178489286, compound

5-(3-Bromo-phenyl)-1H-tetrazole 8b (20 g, 89 mmol) and 2-methoxybenzeneboronic acid (14.2 g, 93.3 mmol) were dissolved in 530 mL of 1,4-dioxane followed by addition of tetrakis(triphenylphosphine)palladium (1.84 g) and sodium carbonate (18.9 g, 178 mmol) under argon atmosphere. The reaction mixture was heated to reflux overnight. The reaction was monitored by TLC until the disappearance of the starting materials. The mixture was concentrated under reduced pressure to remove 1,4-dioxane and then hydrochloric acid (200 mL, 6 mol/L) was added. The mixture was cooled for 2 hours and the layers were separated. The organic layer was collected and concentrated. The residue was dissolved in 500 mL of ethyl acetate and washed with 250 mL of water. The mixture was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was dissolved in 25 mL of ethyl acetate and standing overnight. The mixture was filtered to obtain the title compound 5-(2′-methoxy-biphenyl-3-yl)-1H-tetrazole 8c (15 g, yield 68.2%) as a light yellow solid.

1. temperatureThe reaction mixture was heated
2. temperatureto reflux overnight
3. concentrationThe mixture was concentrated under reduced pressure
4. customto remove 1,4-dioxane
5. additionhydrochloric acid (200 mL, 6 mol/L) was added
6. temperatureThe mixture was cooled for 2 hours
7. customthe layers were separated
8. customThe organic layer was collected
9. concentrationconcentrated
10. dissolutionThe residue was dissolved in 500 mL of ethyl acetate
11. washwashed with 250 mL of water
12. dry with materialThe mixture was dried over anhydrous sodium sulfate
13. concentrationconcentrated under reduced pressure
14. dissolutionThe residue was dissolved in 25 mL of ethyl acetate
15. filtrationThe mixture was filtered

ORD record

ord-0a1f51286c28439397ea96f91c98082b

Source dataset

uspto-grants-2013_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08367710B2