Sodium Carbonate → 3-(6-Isopropyl-quinolin-8-yl)-benzaldehyde

HRID 896653Notes

Reaction equation

HRID 896653 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:12]([CH3:14])[CH3:13])[CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][CH:8]=[CH:7]2.[CH:15]([C:17]1[CH:18]=[C:19](B(O)O)[CH:20]=[CH:21][CH:22]=1)=[O:16].C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.O.C(OCC)(=O)C.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>[CH:12]([C:4]1[CH:5]=[C:6]2[C:11](=[C:2]([C:21]3[CH:22]=[C:17]([CH:18]=[CH:19][CH:20]=3)[CH:15]=[O:16])[CH:3]=1)[N:10]=[CH:9][CH:8]=[CH:7]2)([CH3:14])[CH3:13]

Participants

8

Reactant 3

HCID 10340Sodium CarbonateHCID 27343563-Formylphenylboronic acidHCID 218655558-Bromo-6-(propan-2-yl)quinoline

Product 1

HCID 218655853-(6-Isopropyl-quinolin-8-yl)-benzaldehyde

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 8-bromo-6-isopropyl-quinoline (9.79 g, 39 mmol, described in International Patent Publication WO 94/22852), 3-(formyl)-phenyl-boronic acid (11.7 g, 78 mmol), sodium carbonate (78 mL, 2M, H2O), Pd(Ph3P)4 (2.7 g, 2.3 mmol) in DME (200 mL) was heated at 70° C. for 18 h. The reaction mixture was cooled to 21° C. then diluted with water and ethyl acetate. The organic extracts were washed (H2O, brine), dried (MgSO4), filtered and concentrated. Purification by flash chromatography (eluting with hexane/ethyl acetate, 80:20) provided the title compound.

Workup

  1. temperatureThe reaction mixture was cooled to 21° C.
  2. washThe organic extracts were washed (H2O, brine)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification
  7. washby flash chromatography (eluting with hexane/ethyl acetate, 80:20)

Sources & evidence

ORD record
ord-114bc10da4974579ab1bae36c6d4db76
Source dataset
uspto-grants-2005_07
Patent number
US06919353B2

Reaction notes

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