Potassium Hydroxide → HCID 21834413, compound

HRID 1740938Notes

Reaction equation

HRID 1740938 reaction equation
I[C:2]1[C:3]([CH3:15])=[CH:4][C:5]([NH:8][C:9](=[O:14])[C:10]([CH3:13])([CH3:12])[CH3:11])=[N:6][CH:7]=1.C[Si]([C:20]#[CH:21])(C)C.[OH-].[K+]>O1CCCC1.C(N(CC)CC)C.C(Cl)(Cl)Cl.CO.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.[Cu]I>[C:20]([C:2]1[C:3]([CH3:15])=[CH:4][C:5]([NH:8][C:9](=[O:14])[C:10]([CH3:13])([CH3:12])[CH3:11])=[N:6][CH:7]=1)#[CH:21]

Participants

10

Reactant 3

HCID 14797Potassium HydroxideHCID 66111TrimethylsilylacetyleneHCID 17750196N-(5-Iodo-4-methylpyridin-2-yl)-2,2-dimethylpropanamide

Product 1

HCID 21834413HCID 21834413, compound

Reagents, catalysts & solvents 6

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 887MethanolSolventHCID 6212ChloroformSolventHCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolvent

Procedure

To a mixture of 5-iodo-4-methyl-2-trimethylacetylaminopyridine (176 mg, 0.55 mmol) in tetrahydrofuran (0.60 mL), triethyamine (3.32 mL), bis(triphenylphosphine)palladium(II) chloride (4 mg), copper(I) iodide (1.1 mg) and (trimethylsilyl)acetylene (117 uL, 0.83 mmol) were added. The mixture was stirred at room temperature for 3 h. The mixture was diluted with chloroform (50 mL), dried (Na2SO4), and evaporated to give a tan solid. The crude solid was dissolved in methanol (5 mL), treated with 1N potassium hydroxide (0.61 mL) and stirred at room temperature 18 h. The mixture was evaporated to dryness, dissolved in chloroform (50 mL), dried over Na2SO4, and evaporated to a solid. The product was purified by silica gel column chromatography using 10% ethyl acetate/hexane to yield the title compound.

Workup

  1. additionwere added
  2. dry with materialdried (Na2SO4)
  3. customevaporated
  4. customto give a tan solid
  5. stirringstirred at room temperature 18 h
  6. customThe mixture was evaporated to dryness
  7. dissolutiondissolved in chloroform (50 mL)
  8. dry with materialdried over Na2SO4
  9. customevaporated to a solid
  10. customThe product was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-5c7fcade31324f98bed9d1a3d031ce45
Source dataset
uspto-grants-1999_10
Patent number
US05972975

Reaction notes

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