Dichloromethane → HCID 58099181, compound

HRID 1892993Notes

Reaction equation

HRID 1892993 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.[C:13]1(B(O)O)[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:16]=[CH:15][CH:14]=1.C(=O)([O-])O.[Na+].ClCCl>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.C(OCC)C>[C:21]1([C:2]2[CH:3]=[C:4]3[C:9](=[CH:10][CH:11]=2)[N:8]=[C:7]([CH3:12])[CH:6]=[CH:5]3)[C:22]2[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:18]=[CH:19][CH:20]=1

Participants

9

Reactant 4

HCID 6344DichloromethaneHCID 2545321-Naphthaleneboronic acidHCID 516892Sodium BicarbonateHCID 5228856-Bromo-2-methylquinoline

Product 1

HCID 58099181HCID 58099181, compound

Reagents, catalysts & solvents 4

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 8076Glycol monoethyl etherSolvent3×

Conditions

Temperature
90 °C

Procedure

6-Bromo-2-methylquinoline (32.5; 0.145 mole) was dissolved in 2-ethoxy ethanol (200 ml) and to the magnetically stirred solution under nitrogen was added tetrakis(triphenyl phosphine) palladium (5.1 g; 0.0044 mole) followed by 2-ethoxy ethanol (25 ml). After 5 minutes stirring at room temperature 1-naphthaleneboronic acid (25.0 g; 0.145 mole) was added followed by 2-ethoxyethanol (75 ml). Sodium hydrogencarbonate (35 g; 0.42 mole) in water (200 ml) was added all at once and the reaction mixture was stirred and heated under nitrogen atmosphere at 90° C. for 20 h. After 1 h, the reaction mixture became orange in colour. The reaction mixture was allowed to cool, dichloromethane (100 ml) was added and the reaction mixture was filtered off under suction using celite, with a layer of silica gel on the top. To the filtrate further dichloromethane (250 ml) was added, extracted with de-ionised water (2×300 ml) and finally with brine (250 ml). The organic phase was dried over anhydrous magnesium sulphate and the solvent removed to give a thick liquid. Trituration with diethyl ether and cooling in the refrigerator gave a light yellow solid. The product was dried under vacuum at 80° C., (22 g; 56%). Mp 111° C. (DSC, onset). Elemental analysis: Found C, 89.16; H, 5.58; N, 5.15; C20H15N requires C, 89.19; H, 5.61; and N, 5.20%.

Workup

  1. additionwas added
  2. temperatureto cool
  3. filtrationthe reaction mixture was filtered off under suction
  4. additionTo the filtrate further dichloromethane (250 ml) was added
  5. extractionextracted with de-ionised water (2×300 ml) and finally with brine (250 ml)
  6. dry with materialThe organic phase was dried over anhydrous magnesium sulphate
  7. customthe solvent removed
  8. customto give a thick liquid
  9. customgave a light yellow solid
  10. customThe product was dried under vacuum at 80° C.

Sources & evidence

ORD record
ord-cc1944ae7afd44e1b649039950314344
Source dataset
uspto-grants-2013_08
Patent number
US08507896B2

Reaction notes

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