Cesium carbonate → HCID 89560502, compound

HRID 1747229Notes

Reaction equation

HRID 1747229 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[N:2]1.I[C:7]1[CH:8]=[C:9]([CH:19]=[CH:20][CH:21]=1)[CH2:10][C:11]1([CH3:18])[NH:16][C:15](=[O:17])[CH2:14][O:13][CH2:12]1.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C.[Cu]I>[CH3:18][C:11]1([CH2:10][C:9]2[CH:19]=[CH:20][CH:21]=[C:7]([N:2]3[N:3]=[CH:4][CH:5]=[N:1]3)[CH:8]=2)[NH:16][C:15](=[O:17])[CH2:14][O:13][CH2:12]1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 89561383HCID 89561383, compoundHCID 178418936HCID 178418936, compound

Product 1

HCID 89560502HCID 89560502, compound

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6228DimethylformamideSolvent

Procedure

DMCDA (85 μL, 0.538 mmol) followed by 1H-1,2,3-triazole (0.31 mL, 5.38 mmol) were added to a mixture of rac-5-(3-iodo-benzyl)-5-methyl-morpholin-3-one H-8 (890 mg, 2.69 mmol), Cs2CO3 (1.75 g, 5.38 mmol) and CuI (77 mg, 0.40 mmol) in DMF (5 mL) under argon and the resulting blue suspension was heated to 120° C. for 18 h. The reaction mixture was cooled to RT before being quenched with water and filtered over celite rinsing with water and DCM. The layers were separated and the aqueous phase was re-extracted with DCM (2×). The combined organic extracts were washed with brine, dried over Na2SO4, filtered and evaporated in vacuo. The crude product was purified by flash chromatography (eluting with a gradient of 75% to 100% EtOAc in hexane) to give the title compound as a pale brown solid. LC-MS A: tR=0.69 min; [M+H]+=273.21.

Workup

  1. custombefore being quenched with water
  2. filtrationfiltered
  3. washover celite rinsing with water and DCM
  4. customThe layers were separated
  5. extractionthe aqueous phase was re-extracted with DCM (2×)
  6. washThe combined organic extracts were washed with brine
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. customevaporated in vacuo
  10. customThe crude product was purified by flash chromatography (
  11. washeluting with a gradient of 75% to 100% EtOAc in hexane)

Sources & evidence

ORD record
ord-f546d3d4f23648be9b433db909f66014
Source dataset
uspto-grants-2015_10
Patent number
US09150566B2

Reaction notes

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