1,2-Dimethoxyethane → HCID 23442339, compound

HRID 2119646Notes

Reaction equation

HRID 2119646 reaction equation
Br[C:2]1[C:3]2[C:4](Cl)=[C:5]3[N:14]([CH3:15])[N:13]=[CH:12][C:6]3=[N:7][C:8]=2[CH:9]=[CH:10][CH:11]=1.C[O:18][C:19]1[CH:24]=[CH:23][C:22](B(O)O)=[CH:21][CH:20]=1.C(=O)(O)[O-:29].[Na+].COCCOC>C(OCC)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[OH:18][C:19]1[CH:24]=[CH:23][C:22]([C:2]2[C:3]3[C:4](=[O:29])[C:5]4[N:14]([CH3:15])[N:13]=[CH:12][C:6]=4[NH:7][C:8]=3[CH:9]=[CH:10][CH:11]=2)=[CH:21][CH:20]=1

Participants

7

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 201262(4-Methoxyphenyl)boronic acidHCID 516892Sodium BicarbonateHCID 23442335HCID 23442335, compound

Product 1

HCID 23442339HCID 23442339, compoundYield 60%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 3283Diethyl EtherSolvent

Procedure

A mixture of 8-bromo-9-chloro-1-methyl-1H-pyrazolo[4,3-b]quinoline (EXAMPLE 38, step 1, 100 mg, 0.337 mmol), 4-methoxyphenylboronic acid (56 mg, 0.371 mmol) and dichlorobis(triphenylphosphine)palladium (II) (24 mg, 0.034 mmol) in a mixture of saturated aqueous sodium bicarbonate (0.5 ml) and 1,2-dimethoxyethane (2.5 ml) was refluxed for 5 h. After cooling to room temperature, the mixture was diluted with diethyl ether (100 ml), washed with saturated aqueous sodium bicarbonate (30 ml) and dried over magnesium sulfate. Removal of solvent gave a solid, which was chromatographed on a column of silica gel eluting with ethyl acetate/hexane (1:5) to afford 65 mg (60%) of the title compound as a yellow solid.

Workup

  1. temperaturewas refluxed for 5 h
  2. washwashed with saturated aqueous sodium bicarbonate (30 ml)
  3. dry with materialdried over magnesium sulfate
  4. customRemoval of solvent
  5. customgave a solid, which
  6. customwas chromatographed on a column of silica gel eluting with ethyl acetate/hexane (1:5)

Sources & evidence

ORD record
ord-27a757aeeee44385bffc28d2b54c843f
Source dataset
uspto-grants-2004_02
Patent number
US06686373B2

Reaction notes

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