Triethylamine → HCID 23588013, compound

HRID 416574Notes

Reaction equation

HRID 416574 reaction equation
[CH2:1]([NH:8][C:9]([C:11]1[C:12](=[O:22])[N:13]([CH2:18][CH2:19][CH2:20][CH3:21])[CH:14]=[C:15](I)[CH:16]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:23]1([C:29]#[CH:30])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C(N(CC)CC)C.[Cl-].[NH4+]>CN(C=O)C.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(OCC)(=O)C>[CH2:1]([NH:8][C:9]([C:11]1[C:12](=[O:22])[N:13]([CH2:18][CH2:19][CH2:20][CH3:21])[CH:14]=[C:15]([C:30]#[C:29][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:16]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

9

Reactant 4

HCID 8471TriethylamineHCID 10821PhenylacetyleneHCID 25517Ammonium ChlorideHCID 66632789HCID 66632789, compound

Product 1

HCID 23588013HCID 23588013, compoundYield 89%

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 1-butyl-5-iodo-2-oxo-1,2-dihydropridine-3-carboxylic acid benzylamide (3-067) (78 mg) in DMF (2.0 mL) were added PdCl2(PPh3)2 (15 mg), phenylacetylene (89 mg), CuI (11 mg), and triethylamine (48 mg) at room temperature. After stirred at 90° C. for 18 h, to the reaction mixture were added a saturated aqueous solution of ammonium chloride and ethyl acetate. The organic layer was separated and the aqueous layer was extracted three times with ethyl acetate, and the combined organic layers were washed with water and brine, dried over anhydrous magnesium sulfate, and evaporated under reduced pressure. The obtained crude product was purified by the preparative thin-layer chromatography (toluene/acetone=7/1) to give 1-butyl-2-oxo-5-phenylethynyl-1,2-dihydropridine-3-carboxylic acid benzylamide (3-069) (65 mg, 89%) as an oil.

Workup

  1. customThe organic layer was separated
  2. extractionthe aqueous layer was extracted three times with ethyl acetate
  3. washthe combined organic layers were washed with water and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customevaporated under reduced pressure
  6. customThe obtained crude product
  7. customwas purified by the preparative thin-layer chromatography (toluene/acetone=7/1)

Sources & evidence

ORD record
ord-cecd40d8bbac4496adfac9de9026b8e5
Source dataset
uspto-grants-2012_01
Patent number
US08088924B2

Reaction notes

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