2-Bromo-3-pyridinol → 2-(Trimethylsilyl)furo[3,2-b]pyridine

HRID 1013711Notes

Reaction equation

HRID 1013711 reaction equation
Br[C:2]1[C:7]([OH:8])=[CH:6][CH:5]=[CH:4][N:3]=1.[C:9]([Si:11]([CH3:14])([CH3:13])[CH3:12])#[CH:10]>[Cu]I.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.O1CCOCC1>[CH3:12][Si:11]([CH3:14])([CH3:13])[C:9]1[O:8][C:7]2[C:2](=[N:3][CH:4]=[CH:5][CH:6]=2)[CH:10]=1

Participants

6

Reactant 2

HCID 230702-Bromo-3-pyridinolHCID 66111Trimethylsilylacetylene2×

Product 1

HCID 136365392-(Trimethylsilyl)furo[3,2-b]pyridine

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
50 °C

Procedure

A sealed pressure flask was charged with 2-bromopyridin-3-ol (10.0 g, 57.5 mmol), ethynyltrimethylsilane (15.9 ml, 115 mmol), copper (I) iodide (1.09 g, 5.75 mmol), bis(triphenylphosphine)palladium(II) chloride (2.02 g, 2.87 mmol) and 7.5 mL of dioxane. Ethynyltrimethylsilane (15.9 ml, 115 mmol) and TEA (40.0 ml, 287 mmol) were added, the vial was flushed with nitrogen, and the reaction was stirred at 50° C. for 18 h. The reaction was concentrated and purified via column chromatography (gradient elution 0-40% EtOAc:Hex) to afford 2-(trimethylsilyl)furo[3,2-b]pyridine as a brown oil. MS Found M+H+=192.3

Workup

  1. customthe vial was flushed with nitrogen
  2. concentrationThe reaction was concentrated
  3. custompurified via column chromatography (gradient elution 0-40% EtOAc:Hex)

Sources & evidence

ORD record
ord-8094ac24fd944ee1b12092ababb6d9e8
Source dataset
uspto-grants-2011_07
Patent number
US07981891B2

Reaction notes

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