Sodium Carbonate → HCID 58099177, compound

HRID 1892992Notes

Reaction equation

HRID 1892992 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([CH3:12])[CH:6]=[CH:5]2.[F:13][C:14]1[CH:19]=[C:18]([F:20])[CH:17]=[CH:16][C:15]=1B(O)O.C(OC(O)C)C.C(=O)([O-])[O-].[Na+].[Na+]>C(OCCO)C.O.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[F:13][C:14]1[CH:19]=[C:18]([F:20])[CH:17]=[CH:16][C:15]=1[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([CH3:12])[CH:6]=[CH:5]2

Participants

8

Reactant 4

HCID 10340Sodium CarbonateHCID 5228856-Bromo-2-methylquinolineHCID 27343342,4-Difluorophenylboronic acidHCID 101298981-Ethoxyethanol

Product 1

HCID 58099177HCID 58099177, compound

Reagents, catalysts & solvents 3

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 962WaterSolventHCID 8076Glycol monoethyl etherSolvent

Procedure

To a solution 6-Bromo-2-methylquinoline (4.7 g; 0.021 mol) in 2-ethoxyethanol (80 ml) was added tetrakis(triphenylphosphine) palladium (0.5 g; 0.0004 mol) and the reaction mixture was stirred at room temperature under nitrogen atmosphere for 5 minutes. 2,4-Difluorophenylboronic acid (3.5 g; 0.022 mol) was added followed by ethoxyethanol (20 ml). Sodium carbonate (10 g; 0.094 mol) in water (50 ml) was added and the reaction mixture was magnetically stirred and heated under nitrogen at 90° C. for 16 h. The cooled reaction mixture was filtered through a pad of Celite, hyflo supercel and then extracted with dichloromethane (3×100 ml), after addition of de-ionised water. The organic layer was washed with brine, dried over anhydrous magnesium sulphate and solvent removed to give the residue, which was triturated with ether and cooling in the refrigerator gave a solid. This was filtered off and dried under vacuum at 60° C. to give a colourless solid. Yield 3.9 g (72%). Mp 86° C. (DSC, onset). Elemental analysis: Found C, 73.76; H, 4.39; N, 5.38; C16H11NF2 requires C, 75.28; H, 4.34; and N, 5.49%.

Workup

  1. stirringthe reaction mixture was magnetically stirred
  2. temperatureheated under nitrogen at 90° C. for 16 h
  3. customThe cooled reaction mixture
  4. filtrationwas filtered through a pad of Celite, hyflo supercel
  5. extractionextracted with dichloromethane (3×100 ml)
  6. additionafter addition of de-ionised water
  7. washThe organic layer was washed with brine
  8. dry with materialdried over anhydrous magnesium sulphate and solvent
  9. customremoved
  10. customto give the residue, which
  11. customwas triturated with ether
  12. temperaturecooling in the refrigerator
  13. customgave a solid
  14. filtrationThis was filtered off
  15. customdried under vacuum at 60° C.
  16. customto give a colourless solid

Sources & evidence

ORD record
ord-43a14bf2fc404806a185ddab576160e5
Source dataset
uspto-grants-2013_08
Patent number
US08507896B2

Reaction notes

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