Sodium Bicarbonate → HCID 58099175, compound

HRID 1892995Notes

Reaction equation

HRID 1892995 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.[S:13]1[CH:17]=[CH:16][CH:15]=[C:14]1B(O)O.C(OC(O)C)C.C(=O)([O-])O.[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>[CH3:12][C:7]1[CH:6]=[CH:5][C:4]2[C:9](=[CH:10][CH:11]=[C:2]([C:14]3[S:13][CH:17]=[CH:16][CH:15]=3)[CH:3]=2)[N:8]=1

Participants

8

Reactant 4

HCID 516892Sodium BicarbonateHCID 5228856-Bromo-2-methylquinolineHCID 27339602-Thiopheneboronic acidHCID 101298981-Ethoxyethanol

Product 1

HCID 58099175HCID 58099175, compound

Reagents, catalysts & solvents 3

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

Procedure

To a solution 6-Bromo-2-methylquinoline (17.4 g; 0.078 mol) in 2-ethoxyethanol (100 ml) was added tetrakis(triphenylphosphine) palladium (2.7 g; 0.0023 mol) and the reaction mixture was stirred at room temperature under nitrogen atmosphere for 5 minutes. 2-Thienylboronic acid (10.0 g; 0.078 mol) was added followed by ethoxyethanol (70 ml). Sodium hydrogencarbonate (20 g; 0.24 mol) in water (100 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 (2×150 ml), after addition of de-ionised water. The organic layer was washed with brine, dried over anhydrous magnesium sulphate and solvent removed to give a light brown liquid. The liquid was distilled under reduced pressure to remove ethoxy ethanol. The residue was triturated with diethyl ether and cooled in the refrigerator to give an off white solid, 10.6 g (61%); Mp 87° C. (DSC, onset). Elemental analysis: Found C, 74.72; H 4.92; N, 6.12; S 13.43; C14H11NS requires C, 74.63; H 4.92; N, 6.21; and S, 14.24%.

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 (2×150 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 a light brown liquid
  11. distillationThe liquid was distilled under reduced pressure
  12. customto remove ethoxy ethanol
  13. customThe residue was triturated with diethyl ether
  14. temperaturecooled in the refrigerator
  15. customto give an off white solid, 10.6 g (61%)

Sources & evidence

ORD record
ord-635486f3150846fe808756ec86d80f15
Source dataset
uspto-grants-2013_08
Patent number
US08507896B2

Reaction notes

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