Cesium carbonate → HCID 67455564, compound

HRID 469747Notes

Reaction equation

HRID 469747 reaction equation
[C:1]([O:5][C:6]([C@@H:8]1[CH2:12][CH2:11][C:10](=[O:13])[NH:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Br[C:15]1[CH:20]=[CH:19][C:18]([F:21])=[CH:17][N:16]=1.C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2>>[C:1]([O:5][C:6]([C@@H:8]1[CH2:12][CH2:11][C:10](=[O:13])[N:9]1[C:15]1[CH:20]=[CH:19][C:18]([F:21])=[CH:17][N:16]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 4

HCID 10796Cesium carbonateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 27831712-Bromo-5-fluoropyridineHCID 10888648tert-Butyl 5-oxo-L-prolinate

Product 1

HCID 67455564HCID 67455564, compoundYield 6%

Conditions

Temperature
120 °C

Procedure

To a pressure tube containing (S)-5-oxo-pyrrolidine-2-carboxylic acid tert-butyl ester (0.5 g, 2.699 mmol), 2-bromo-5-fluoropyridine (0.57 g, 3.239 mmol), cesium carbonate (1.231 g, 3.779 mmol), Xantphos (0.156 g, 0.27 mmol), and tris (dibenzylideneacetone)palladium (0) (0.247 g, 0.27 mmol) is added 13.5 mL degassed anhydrous 1,4-dioxane. The mixture is heated at 120° C. under an atmosphere of Argon overnight. The solution is cooled to room temperature, filtered through Celite®, and concentrated under reduced pressure. The crude material is purified by flash chromatography eluting product with 305 ethyl acetate/heptanes. The product fractions are pooled and concentrated under reduced pressure to afford 45 mg of title compound. Yield 6%. ESI m/z 225=MH+

Workup

  1. customdegassed anhydrous 1,4-dioxane
  2. temperatureThe solution is cooled to room temperature
  3. filtrationfiltered through Celite®
  4. concentrationconcentrated under reduced pressure
  5. customThe crude material is purified by flash chromatography
  6. washeluting product with 305 ethyl acetate/heptanes
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-24e0ed0b15094d5bba10bc46edc8ba0d
Source dataset
uspto-grants-2014_01
Patent number
US08629157B2

Reaction notes

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