Water → HCID 13081737, compound

HRID 1640041Notes

Reaction equation

HRID 1640041 reaction equation
Br[C:2]1[CH:3]=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.[CH3:12][Si:13]([C:16]#[CH:17])([CH3:15])[CH3:14].O>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.CCOCC>[CH3:12][Si:13]([C:16]#[C:17][C:2]1[CH:3]=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2)([CH3:15])[CH3:14]

Participants

6

Reactant 3

HCID 962WaterHCID 214133-BromoquinolineHCID 66111Trimethylsilylacetylene

Product 1

HCID 13081737HCID 13081737, compound

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 3283Diethyl EtherSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 3-bromoquinoline (10.40 g, 0.05 mol), trimethylsilylacetylene (8.48 mL, 0.06 mol), cuprous iodide (0.5 g) and trans-dichlorobis(triphenylphosphine)palladium (1 g) and TEA (15 mL) was heated at 70° C. in a sealed tube for 1 h. H2O (150 mL) was added, followed by Et2O (300 mL). The organic layer was separated and the aqueous layer extracted with Et2O (200 mL). The combined organic layers were dried (Na2SO4) and concentrated. The residue was purified by flash column chromatography (eluent: 100% DCM) to give 3-(trimethylsilylethynyl) quinoline as a brown oil. 3-(Trimethylsilylethynyl) quinoline was dissolved in anhydrous MeOH (100 mL) and K2CO3 (0.69 g, 5 mmol) was added. The mixture was stirred at rt for 1 h and DCM (250 mL) was added. The mixture was filtered over celite. The filtrate was evaporated and the residue was purified by flash column chromatography to give Compound 13b as an off-white solid.

Workup

  1. customThe organic layer was separated
  2. extractionthe aqueous layer extracted with Et2O (200 mL)
  3. dry with materialThe combined organic layers were dried (Na2SO4)
  4. concentrationconcentrated
  5. customThe residue was purified by flash column chromatography (eluent: 100% DCM)

Sources & evidence

ORD record
ord-cd97f229df134d3e807ca914ef989345
Source dataset
uspto-grants-2012_02
Patent number
US08110683B2

Reaction notes

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