Water → HCID 22504411, compound

HRID 1432283Notes

Reaction equation

HRID 1432283 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-b134e8d738d948eea66230e7f0f1eb88
Source dataset
uspto-grants-2009_11
Patent number
US07612070B2

Reaction notes

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