Potassium Phosphate, Tribasic → HCID 117776714, compound

HRID 1477459Notes

Reaction equation

HRID 1477459 reaction equation
Br[C:2]1[CH:24]=[CH:23][C:5]([CH2:6][N:7]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10](=[O:17])[C:9]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:8]2)=[CH:4][CH:3]=1.[O:25]1[CH2:30][CH2:29][CH2:28][CH2:27][CH:26]1[N:31]1[C:35](B2OC(C)(C)C(C)(C)O2)=[CH:34][CH:33]=[N:32]1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>COCCOC.O.C(OCC)(=O)C.C1C=CC(P([C]2[CH][CH][CH][CH]2)C2C=CC=CC=2)=CC=1.C1C=CC(P([C]2[CH][CH][CH][CH]2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl.[Fe]>[O:17]=[C:10]1[C:11]2[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=2)[N:7]([CH2:6][C:5]2[CH:23]=[CH:24][C:2]([C:35]3[N:31]([CH:26]4[CH2:27][CH2:28][CH2:29][CH2:30][O:25]4)[N:32]=[CH:33][CH:34]=3)=[CH:3][CH:4]=2)[CH:8]=[C:9]1[C:18]([O:20][CH2:21][CH3:22])=[O:19]

Participants

7

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 115872081-(tetrahydro-2H-pyran-2-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 23635027HCID 23635027, compound

Product 1

HCID 117776714HCID 117776714, compoundYield 39%

Reagents, catalysts & solvents 3

HCID 178477754HCID 178477754, compoundCatalystHCID 8857Ethyl AcetateSolventHCID 18180031Water 1,2-dimethoxyethaneSolvent

Conditions

Temperature
100 °C

Procedure

To a suspension of ethyl 1-(4-bromobenzyl)-4-oxo-1,4-dihydroquinoline-3-carboxylate (0.8 g) known from a document (Journal of Medicinal Chemistry, 2007, 50, 5471), 1-(tetrahydro-2H-pyran-2-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (0.86 g) and potassium phosphate (1.1 g) in DME-water (4:1, 20 mL) was added [1,1-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (0.08 g), and the mixture was stirred at 100° C. for 1 hr under microwave irradiation. The reaction mixture was diluted with ethyl acetate, and the insoluble material was filtered off. The filtrate was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated. The residue was purified by silica gel chromatography (hexane-ethyl acetate) to give the title compound (0.37 g) as a pale-yellow solid.

Workup

  1. filtrationthe insoluble material was filtered off
  2. washThe filtrate was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel chromatography (hexane-ethyl acetate)

Sources & evidence

ORD record
ord-02787e40dd4d4a3cbf3ddde99c992ce2
Source dataset
uspto-grants-2016_08
Patent number
US09403802B2

Reaction notes

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