Potassium Phosphate, Tribasic → HCID 70984209, compound

HRID 338872Notes

Reaction equation

HRID 338872 reaction equation
Br[C:2]1[C:3]([F:13])=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([CH3:12])[CH:8]=[CH:7]2.P([CH:27]1[CH2:32][CH2:31]CCC1)(C1CCCCC1)C1CCCCC1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].C1(B(O)O)CC1>C1(C)C=CC=CC=1.O.CC([O-])=O.CC([O-])=O.[Pd+2].C(OCC)(=O)C>[CH:31]1([C:2]2[C:3]([F:13])=[CH:4][CH:5]=[C:6]3[C:11]=2[N:10]=[C:9]([CH3:12])[CH:8]=[CH:7]3)[CH2:32][CH2:27]1

Participants

9

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 75806TricyclohexylphosphineHCID 2760897Cyclopropylboronic acidHCID 70983494HCID 70983494, compound

Product 1

HCID 70984209HCID 70984209, compoundYield 842.6%

Reagents, catalysts & solvents 4

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolvent2×HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 8-bromo-7-fluoro-2-methylquinoline (1.00 g, 4.17 mmol), Pd(OAc)2 (0.047 g, 0.21 mmol), P(Cy)3 (0.13 g, 0.46 mmol), K3PO4 (3.09 g, 14.6 mmol) and cyclopropylboronic acid (0.72 g, 8.33 mmol) in toluene (20 mL) and water (2 mL) was stirred at 100° C. for 8 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. The residue was purified by flash chromatography (3:1 hexane/DCM) to give 8-cyclopropyl-7-fluoro-2-methylquinoline (0.78 g, 92.7%) 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
  6. customThe residue was purified by flash chromatography (3:1 hexane/DCM)

Sources & evidence

ORD record
ord-b5c7260d69064d49a1193c4256dd9858
Source dataset
uspto-grants-2014_11
Patent number
US08889704B2

Reaction notes

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