Sodium Carbonate → HCID 178489286, compound

HRID 384312Notes

Reaction equation

HRID 384312 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:8]2[NH:12][N:11]=[N:10][N:9]=2)[CH:5]=[CH:6][CH:7]=1.[CH3:13][O:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1B(O)O.C(=O)([O-])[O-].[Na+].[Na+]>O1CCOCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:13][O:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]2[NH:12][N:11]=[N:10][N:9]=2)[CH:3]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 27339582-Methoxyphenylboronic acidHCID 178419385HCID 178419385, compound

Product 1

HCID 178489286HCID 178489286, compoundYield 68.2%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-0a1f51286c28439397ea96f91c98082b
Source dataset
uspto-grants-2013_02
Patent number
US08367710B2

Reaction notes

Loading…