Ethyl Acetate → HCID 70984030, compound

HRID 338874Notes

Reaction equation

HRID 338874 reaction equation
Br[C:2]1[C:11]([O:12][CH3:13])=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([CH3:14])=[N:9]2)=[CH:4][CH:3]=1.P([CH:28]1[CH2:33][CH2:32]CCC1)(C1CCCCC1)C1CCCCC1.C1(B(O)O)CC1.C(OCC)(=O)C>C1(C)C=CC=CC=1.O.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH:32]1([C:2]2[C:11]([O:12][CH3:13])=[C:10]3[C:5]([CH:6]=[CH:7][C:8]([CH3:14])=[N:9]3)=[CH:4][CH:3]=2)[CH2:33][CH2:28]1

Participants

8

Reactant 4

HCID 8857Ethyl AcetateHCID 75806TricyclohexylphosphineHCID 2760897Cyclopropylboronic acidHCID 70983053HCID 70983053, compound

Product 1

HCID 70984030HCID 70984030, compoundYield 895.1%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolvent2×HCID 1140TolueneSolvent

Procedure

A solution of 7-bromo-8-methoxy-2-methylquinoline (1.00 g, 3.97 mmol), Pd(OAc)2 (0.045 g, 0.198 mmol), P(Cy)3 (0.122 g, 0.44 mmol) and cyclopropylboronic acid (0.68 g, 7.93 mmol) in toluene (4 mL) and water (0.4 mL) was stirred at 100° C. for 6 hours. After cooling to ambient temperature, ethyl acetate (20 mL) and water (5 mL) were added. The organic layer was separated, washed with brine, dried (sodium sulfate), filtered and concentrated under reduced pressure to give 7-cyclopropyl-8-methoxy-2-methylquinoline (0.84 g, 99%) as an oil.

Workup

  1. customThe organic layer was separated
  2. washwashed with brine
  3. dry with materialdried (sodium sulfate)
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-47dba31eaab84b3e91ac4b1daac37dbe
Source dataset
uspto-grants-2014_11
Patent number
US08889704B2

Reaction notes

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