Potassium Phosphate, Tribasic → HCID 136359761, compound

HRID 1754555Notes

Reaction equation

HRID 1754555 reaction equation
BrC1C=CC2C3N(C[O:17][CH2:18][CH2:19][Si:20]([CH3:23])([CH3:22])[CH3:21])N=CC=3C(=O)NC=2C=1.BrC1C=CC2C3NN(COCC[Si](C)(C)C)CC=3C(=O)NC=2C=1.CC1(C)C(C)(C)OB(C2C=CN=CC=2)O1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].[N:70]1[CH:75]=[CH:74][C:73]([C:76]2[CH:77]=[CH:78][C:79]3[C:80]4[NH:89][N:88](OCC[Si](C)(C)C)[CH2:87][C:81]=4[C:82](=[O:86])[NH:83][C:84]=3[CH:85]=2)=[CH:72][CH:71]=1>CN(C=O)C.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[N:70]1[CH:75]=[CH:74][C:73]([C:76]2[CH:77]=[CH:78][C:79]3[C:80]4[N:89]([O:17][CH2:18][CH2:19][Si:20]([CH3:23])([CH3:22])[CH3:21])[N:88]=[CH:87][C:81]=4[C:82](=[O:86])[NH:83][C:84]=3[CH:85]=2)=[CH:72][CH:71]=1

Participants

8

Reactant 5

HCID 62657Potassium Phosphate, TribasicHCID 27346484-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridineHCID 86679797HCID 86679797, compoundHCID 86679798HCID 86679798, compoundHCID 136359762HCID 136359762, compound

Product 1

HCID 136359761HCID 136359761, compound

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
150 °C

Procedure

To a solution of 7-bromo-1-{[2-(trimethylsilyl)ethoxy]methyl}-1,5-dihydro-4H-pyrazolo[4,3-c]quinolin-4-one and 7-bromo-2-{[2-(trimethylsilyl)ethoxy]methyl}-1,5-dihydro-4H-pyrazolo[4,3-c]quinolin-4-one [described in Step 3.1] (18.2 g, 46.2 mmol) in 150 mL of DMF placed in a microwave reactor are successively added 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (11.4 g, 55.4 mmol), aqueous 2M K3PO4 solution (47 mL, 92.4 mmol) and the catalyst PdCl2(dppf) (1.88 g, 2.31 mmol) under nitrogen. The reactor is sealed and the reaction mixture is stirred for 20 minutes at 150° C. under microwave irradiation. After concentrating the reaction mixture, purification by flash chromatography on silica (DCM/MeOH: 0/100 to 95/5) gives 12.4 g of 7-(pyrid-4-yl)-1-[2-(trimethylsilyl)ethoxy]-1,5-dihydro-4H-pyrazolo[4,3-c]quinolin-4-one and 7-(pyrid-4-yl)-2-[2-(trimethylsilyl)ethoxy]-1,5-dihydro-4H-pyrazolo[4,3-c]quinolin-4-one in the form of a white solid (yield: 54%).

Workup

  1. customThe reactor is sealed
  2. concentrationAfter concentrating
  3. customthe reaction mixture, purification by flash chromatography on silica (DCM/MeOH: 0/100 to 95/5)

Sources & evidence

ORD record
ord-003268ceb22f4ce780c370d0d47dd4b1
Source dataset
uspto-grants-2015_10
Patent number
US09169246B2

Reaction notes

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