Dichloromethane → HCID 58099169, compound

HRID 1892994Notes

Reaction equation

HRID 1892994 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:26]2[C:27]3=[C:28]4[C:23](=[CH:24][CH:25]=2)[CH:22]=[CH:21][CH:20]=[C:19]4[CH:18]=[CH:17][C:16]3=[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:20]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:19]2[C:28]3=[C:27]4[C:16](=[CH:17][CH:18]=2)[CH:15]=[CH:14][CH:13]=[C:26]4[CH:25]=[CH:24][C:23]3=[CH:22][CH:21]=1

Participants

8

Reactant 4

HCID 6344DichloromethaneHCID 516892Sodium BicarbonateHCID 5228856-Bromo-2-methylquinolineHCID 5084102Pyren-1-ylboronic acid

Product 1

HCID 58099169HCID 58099169, compound

Reagents, catalysts & solvents 3

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 962WaterSolventHCID 8076Glycol monoethyl etherSolvent2×

Procedure

6-Bromo-2-methylquinoline (4.5; 20 mmole) was dissolved in 2-ethoxy ethanol (30 ml) and to the magnetically stirred solution under nitrogen was added tetrakis(triphenyl phosphine) palladium (1 g; 0.9 mmole). After 5 minutes stirring at room temperature, 1-pyreneboronic acid (5.0 g; 20 mmole) was added followed by 2-ethoxyethanol (10 ml). Sodium hydrogencarbonate (10 g; 94 mmole) in water (60 ml) was added all at once and the reaction mixture was stirred and heated under nitrogen atmosphere at 90° C. for 18 h. The reaction mixture was allowed to cool, dichloromethane (100 ml) was added and the reaction mixture was filtered through a layer of silica gel. To the filtrate further dichloromethane (50 ml) was added and extracted with de-ionised water (2×100 ml). The organic phase was dried over anhydrous magnesium sulphate and the solvent removed to give the required product. The product was dried under vacuum at 80° C., Yield 4.5 g (67%). Mp 133° C. (DSC, onset). Elemental analysis: Found C, 90.80; H, 5.09; N, 4.32; C26H17N requires C, 90.93; H, 4.99; and N, 4.08%.

Workup

  1. stirringwas stirred
  2. temperatureheated under nitrogen atmosphere at 90° C. for 18 h
  3. temperatureto cool
  4. filtrationthe reaction mixture was filtered through a layer of silica gel
  5. additionTo the filtrate further dichloromethane (50 ml) was added
  6. extractionextracted with de-ionised water (2×100 ml)
  7. dry with materialThe organic phase was dried over anhydrous magnesium sulphate
  8. customthe solvent removed

Sources & evidence

ORD record
ord-048ef74e9c3b4428821df651cf7c4406
Source dataset
uspto-grants-2013_08
Patent number
US08507896B2

Reaction notes

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