Triethylamine → HCID 22504425, compound

HRID 1814128Notes

Reaction equation

HRID 1814128 reaction equation
[CH3:1][Si:2]([C:5]#[CH:6])([CH3:4])[CH3:3].[C:7]1([S:13]([NH:16][C:17]2[C:22](I)=[CH:21][C:20]([S:24][CH3:25])=[CH:19][N:18]=2)(=[O:15])=[O:14])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C(N(CC)CC)C.O1CCOCC1>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.C(OCC)(=O)C.O>[C:7]1([S:13]([N:16]2[C:17]3=[N:18][CH:19]=[C:20]([S:24][CH3:25])[CH:21]=[C:22]3[CH:6]=[C:5]2[Si:2]([CH3:4])([CH3:3])[CH3:1])(=[O:14])=[O:15])[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 312751,4-DioxaneHCID 66111TrimethylsilylacetyleneHCID 154868512-Benzenesulfonylamino-3-iodo-5-methylthiopyridine

Product 1

HCID 22504425HCID 22504425, compoundYield 80.3%

Reagents, catalysts & solvents 3

HCID 178418476HCID 178418476, compoundCatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of trimethylsilylacetylene (0.41 g), 2-benzenesulfonylamino-3-iodo-5-methylthiopyridine (0.82 g), triethylamine (0.42 g), cuprous iodide (30 mg), dichlorobis(triphenylphosphine)palladium (75 mg) and dioxane (2 ml) was stirred at 70° C. for 16 hours under nitrogen atmosphere. To the reaction solution were then added water and ethyl acetate. The insolubles were filtered off. To the filtrate was added a saturated aqueous sodium hydrogencarbonate solution, and the mixture was extracted with ethyl acetate, dried over anhydrous sodium sulfate, filtered and concentrated. The resulting residue was subjected to silica gel column chromatography (hexane:ethyl acetate=10:1) to obtain 0.61 g of the desired product.

Workup

  1. filtrationThe insolubles were filtered off
  2. additionTo the filtrate was added a saturated aqueous sodium hydrogencarbonate solution
  3. extractionthe mixture was extracted with ethyl acetate
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-f8163d7fc25144dabd1d0358b55e7158
Source dataset
uspto-grants-2005_04
Patent number
US06875770B2

Reaction notes

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