Cesium carbonate → HCID 57466830, compound

HRID 601634Notes

Reaction equation

HRID 601634 reaction equation
[C:1]([O:5][C:6](=[O:15])[NH:7][CH2:8][CH2:9][C:10]1[NH:14][N:13]=[N:12][N:11]=1)([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:23][CH2:24][F:25]>CN(C=O)C>[C:1]([O:5][C:6](=[O:15])[NH:7][CH2:8][CH2:9][C:10]1[N:14]([CH2:23][CH2:24][F:25])[N:13]=[N:12][N:11]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 129822-Fluoroethyl bromideHCID 178453348HCID 178453348, compound

Product 1

HCID 57466830HCID 57466830, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution comprising [2-(1H-Tetrazol-5-yl)-ethyl]-carbamic acid tert-butyl ester (EP 449523) (0.125 g, 0.586 mmol) in DMF (5 ml) is added caesium carbonate (0.23 g, 0.703 mmol) followed by 1-bromo-2-fluoroethane (0.174 ml, 2.344 mmol) and the reaction mixture is left to stir at room temperature for 3 days. The solvent is removed in vacuo and the crude residue is purified by flash silica chromatography (elution 3:2 increasing to 1:4 hexane/ethyl acetate) to afford the titled compound and {2-[1-(2-Fluoro-ethyl)-1H-tetrazol-5-yl]-ethyl}-carbamic acid tert-butyl ester.

Workup

  1. waitthe reaction mixture is left
  2. customThe solvent is removed in vacuo
  3. customthe crude residue is purified by flash silica chromatography (elution 3:2 increasing to 1:4 hexane/ethyl acetate)

Sources & evidence

ORD record
ord-fa8945977530468aac78c07e851a36e8
Source dataset
uspto-grants-2011_03
Patent number
US07902375B2

Reaction notes

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