Water → HCID 22504411, compound

HRID 1838396Notes

Reaction equation

HRID 1838396 reaction equation
[NH2:1][C:2]1[C:7](Br)=[N:6][C:5]([S:9][CH3:10])=[CH:4][N:3]=1.[CH2:11]([OH:14])[C:12]#[CH:13].C(N(CC)CC)C.O>O1CCOCC1.[Cu]I>[NH2:1][C:2]1[C:7]([C:13]#[C:12][CH2:11][OH:14])=[N:6][C:5]([S:9][CH3:10])=[CH:4][N:3]=1

Participants

7

Reactant 4

HCID 962WaterHCID 7859Propargyl alcoholHCID 8471TriethylamineHCID 22504391HCID 22504391, compound

Product 1

HCID 22504411HCID 22504411, compoundYield 88.9%

Reagents, catalysts & solvents 2

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

Conditions

Temperature
70 °C

Procedure

To a solution of the compound obtained in Example 34 (2) (440 mg) in dioxane (10 ml), 2-propyn-1-ol (168 mg), bistriphenylphosphine palladium dichloride (72 mg), copper(I) iodide (38 mg) and triethylamine (304 mg) were added successively and the mixture was stirred in a sealed tube at 70° C. for 2 hours. After cooling, the reaction solution was poured into water, and the mixture was extracted with chloroform, dried over anhydrous magnesium sulfate, filtered and concentrated. The resulting residue was separated using silica gel column chromatography (chloroform:methanol=10:1) to obtain 347 mg (88.9%) of the desired product as a brown oil.

Workup

  1. temperatureAfter cooling
  2. extractionthe mixture was extracted with chloroform
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe resulting residue was separated

Sources & evidence

ORD record
ord-566e28f63a4949e69641568098da1ee9
Source dataset
uspto-grants-2004_01
Patent number
US06673797B1

Reaction notes

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