Triethylamine → HCID 53882369, compound

HRID 651654Notes

Reaction equation

HRID 651654 reaction equation
I[C:2]1[C:7]([OH:8])=[CH:6][CH:5]=[CH:4][N:3]=1.[C:9]([O:13][C:14](=[O:25])[NH:15][C@H:16]1[CH2:20][CH2:19][N:18]([CH2:21][C:22]#[CH:23])[C:17]1=[O:24])([CH3:12])([CH3:11])[CH3:10].C(N(CC)CC)C>C(#N)C.O.CCOC(C)=O.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)I>[C:9]([O:13][C:14](=[O:25])[NH:15][C@H:16]1[CH2:20][CH2:19][N:18]([CH2:21][C:22]2[O:8][C:7]3[C:2](=[N:3][CH:4]=[CH:5][CH:6]=3)[CH:23]=2)[C:17]1=[O:24])([CH3:12])([CH3:10])[CH3:11]

Participants

9

Reactant 3

HCID 8471TriethylamineHCID 971792-Iodopyridin-3-olHCID 53895069HCID 53895069, compound

Product 1

HCID 53882369HCID 53882369, compound

Reagents, catalysts & solvents 5

HCID 83717Copper iodideCatalystHCID 178418476HCID 178418476, compoundCatalystHCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 2-iodo-3-hydroxy-pyridine (0.44 g, 2 mmol), (2-oxo-1-prop-2-ynyl-pyrrolidin-3-(S)-yl)-carbamic acid tert-butyl ester (0.6 g, 2.5 mmol), bis(triphenylphosphine)-palladium(II) chloride (Pd(PPh3)2Cl2) (50 mg), copper iodide (25 mg) and triethylamine (3 mL) in 3 mL of acetonitrile is heated in a sealed tube at 120° C. for 2 hours. After cooling, the reaction mixture is diluted with water and EtOAc and the layers are separated. The aqueous layer is extracted with EtOAc. The combined organic layers are washed with water and saturated NaCl solution, then dried over MgSO4, filtered and concentrated. The crude product is purified by column chromatography eluting with a gradient of 25% EtOAc/CH2Cl2 to 90% EtOAc/CFH2Cl2 to yield the title compound as a white solid.

Workup

  1. temperatureAfter cooling
  2. customthe layers are separated
  3. extractionThe aqueous layer is extracted with EtOAc
  4. washThe combined organic layers are washed with water and saturated NaCl solution
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude product is purified by column chromatography
  9. washeluting with a gradient of 25% EtOAc/CH2Cl2 to 90% EtOAc/CFH2Cl2

Sources & evidence

ORD record
ord-ebd828c7abbd4b2ba7ac10700b1e7e27
Source dataset
uspto-grants-2001_08
Patent number
US06281227B1

Reaction notes

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