Lithium Chloride → HCID 23442376, compound

HRID 2119645Notes

Reaction equation

HRID 2119645 reaction equation
Br[C:2]1[C:11]2[NH:10][C:9]3[CH:12]=[N:13][N:14]([CH3:15])[C:8]=3[C:7](=[O:16])[C:6]=2[CH:5]=[CH:4][CH:3]=1.C([Sn](CCCC)(CCCC)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)CCC.[Cl-].[Li+]>O1CCOCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:15][N:14]1[C:8]2[C:7](=[O:16])[C:6]3[CH:5]=[CH:4][CH:3]=[C:2]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)[C:11]=3[NH:10][C:9]=2[CH:12]=[N:13]1

Participants

6

Reactant 3

HCID 433294Lithium ChlorideHCID 607632TributylphenyltinHCID 12985703HCID 12985703, compound

Product 1

HCID 23442376HCID 23442376, compoundYield 34.3%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Procedure

A mixture of 5-bromo-1-methyl-1,4-dihydro-9H-pyrazolo[4,3-b]quinolin-9-one (EXAMPLE 5, 50 mg, 0.18 mmol), tributylphenyltin (0.12 ml, 0.36 mmol), tetrakis(triphenylphosphine)palladium (0) (62 mg, 0.054 mmol) and lithium chloride (19 mg, 0.45 mmol) in 1,4-dioxane (2 ml) was refluxed for 16 h. After cooling to room temperature, the mixture was evaporated, dissolved in ethyl acetate (20 ml) and the insoluble material was filtered off. The filtrate was concentrated in vacuo and purified by preparative thin layer chromatography developing with ethyl acetate/hexane (1/2). The obtained solid was recrystallized from diethyl ether to afford 17 mg (33%) of the title compound as a solid.

Workup

  1. temperaturewas refluxed for 16 h
  2. customthe mixture was evaporated
  3. dissolutiondissolved in ethyl acetate (20 ml)
  4. filtrationthe insoluble material was filtered off
  5. concentrationThe filtrate was concentrated in vacuo
  6. custompurified by preparative thin layer chromatography
  7. customThe obtained solid was recrystallized from diethyl ether

Sources & evidence

ORD record
ord-dc5ca70dbfca4a3b85490f954869954a
Source dataset
uspto-grants-2004_02
Patent number
US06686373B2

Reaction notes

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