Cesium carbonate → HCID 58292620, compound

HRID 1798216Notes

Reaction equation

HRID 1798216 reaction equation
[CH2:1]([O:3][C:4](=[O:18])[CH2:5][CH:6]1[O:10][B:9]([OH:11])[C:8]2[CH:12]=[C:13]([OH:17])[CH:14]=[C:15]([F:16])[C:7]1=2)[CH3:2].C(=O)([O-])[O-].[Cs+].[Cs+].Cl[C:26]1[CH:31]=[N:30][CH:29]=[CH:28][N:27]=1>CN(C=O)C>[CH2:1]([O:3][C:4](=[O:18])[CH2:5][CH:6]1[O:10][B:9]([OH:11])[C:8]2[CH:12]=[C:13]([O:17][C:26]3[CH:31]=[N:30][CH:29]=[CH:28][N:27]=3)[CH:14]=[C:15]([F:16])[C:7]1=2)[CH3:2]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 73277ChloropyrazineHCID 58292615HCID 58292615, compound

Product 1

HCID 58292620HCID 58292620, compoundYield 76.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of ethyl-2-(4-fluoro-1,6-dihydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-3-yl)acetate (0.25 g, 1.0 mmol), cesium carbonate (0.65 g, 2.0 mmol) and 2-chloropyrazine (0.17 g, 1.5 mmol) in DMF (3 mL) was heated to 90° C. for 3 hr. The reaction mixture was concentrated in vacuo and the residue was purified by column chromatography (EtOAc/PE=1/2) on silica gel to give the title compound as a light yellow solid (0.25 g, Yield: 76.7%). MS (ESI) m/z=333 [M+H]+.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe residue was purified by column chromatography (EtOAc/PE=1/2) on silica gel

Sources & evidence

ORD record
ord-253343f6d49c45d9bea1f3a431057625
Source dataset
uspto-grants-2013_01
Patent number
US08343944B2

Reaction notes

Loading…