Cesium carbonate → HCID 58459771, compound

HRID 1675353Notes

Reaction equation

HRID 1675353 reaction equation
Cl[C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][N:3]=1.[CH2:13]1[C:17]2[CH2:18][NH:19][CH2:20][C:16]=2[CH2:15][N:14]1[C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[CH2:9]([O:8][C:6]([C:5]1[CH:11]=[CH:12][C:2]([N:19]2[CH2:18][C:17]3[CH2:13][N:14]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:15][C:16]=3[CH2:20]2)=[N:3][CH:4]=1)=[O:7])[CH3:10]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 2799611Ethyl 6-chloronicotinateHCID 45792434HCID 45792434, compound

Product 1

HCID 58459771HCID 58459771, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Ethyl 6-chloronicotinate (567 mg, 3.05 mmol), tert-butyl 3,4,5,6-tetrahydro-1H-pyrrolo-[3,4-c]pyrrole-2-carboxylate (565.9 mg, 2.7 mmol) and cesium carbonate (878 mg, 2.7 mmol) were stirred in 20 ml of DMF at 100° C. for 8 h and at 120° C. for 8 h. The residue was filtered off, washed with water and ethyl acetate, and dried. The first filtrate was concentrated and stirred with ethyl acetate, and the product was filtered off. Yield: 72%, M+H+: 360.20.

Workup

  1. filtrationThe residue was filtered off
  2. washwashed with water and ethyl acetate
  3. customdried
  4. concentrationThe first filtrate was concentrated
  5. filtrationthe product was filtered off

Sources & evidence

ORD record
ord-8c3dda4afb6c43f2b34fab46d87bd0e0
Source dataset
uspto-grants-2011_08
Patent number
US08003677B2

Reaction notes

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