Cesium carbonate → HCID 90094093, compound

HRID 1753061Notes

Reaction equation

HRID 1753061 reaction equation
[I:1][C:2]1[C:6]2[CH:7]=[N:8][CH:9]=[CH:10][C:5]=2[NH:4][CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[O:17]1[CH2:20][CH:19](OS(C(F)(F)F)(=O)=O)[CH2:18]1>CN(C=O)C>[I:1][C:2]1[C:6]2[CH:7]=[N:8][CH:9]=[CH:10][C:5]=2[N:4]([CH:19]2[CH2:20][O:17][CH2:18]2)[CH:3]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 116873853-IODO-1H-PYRROLO[3,2-C]PYRIDINEHCID 717585431,1,1-trifluoro-3-oxetanyl Methanesulfonic acid ester

Product 1

HCID 90094093HCID 90094093, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 3-iodo-1H-pyrrolo[3,2-c]pyridine (Preparation 47, 2 g, 8.2 mmol) in DMF (150 mL) was added cesium carbonate (24 g, 73.8 mmol) and the mixture stirred for 20 minutes at room temperature. A solution of trifluoromethanesulfonic acid oxetan-3-yl ester (Preparation 54, 8.45 g, 41 mmol) in DMF (15 mL) was added and the reaction stirred at room temperature for 16 hours. The reaction was filtered, and the filtrate concentrated in vacuo. The residue was purified using silica gel column chromatography eluting with 0-5% MeOH in DCM to give a solid that was further washed with EtOAc:Heptane to afford the title compound. (4.46 g, 36%).

Workup

  1. stirringthe reaction stirred at room temperature for 16 hours
  2. filtrationThe reaction was filtered
  3. concentrationthe filtrate concentrated in vacuo
  4. customThe residue was purified
  5. washeluting with 0-5% MeOH in DCM
  6. customto give a solid
  7. washthat was further washed with EtOAc

Sources & evidence

ORD record
ord-46db19ec1c6948ee981576f886db0238
Source dataset
uspto-grants-2015_10
Patent number
US09163021B2

Reaction notes

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