Cesium carbonate → HCID 58292770, compound

HRID 1798243Notes

Reaction equation

HRID 1798243 reaction equation
[OH:1][B:2]1[C:6]2[CH:7]=[C:8]([OH:13])[CH:9]=[C:10]([O:11][CH3:12])[C:5]=2[CH:4]([CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])[O:3]1.C(=O)([O-])[O-].[Cs+].[Cs+].Cl[C:27]1[CH:32]=[N:31][CH:30]=[CH:29][N:28]=1>CN(C=O)C>[CH2:18]([O:17][C:15](=[O:16])[CH2:14][CH:4]1[O:3][B:2]([OH:1])[C:6]2[CH:7]=[C:8]([O:13][C:27]3[CH:32]=[N:31][CH:30]=[CH:29][N:28]=3)[CH:9]=[C:10]([O:11][CH3:12])[C:5]1=2)[CH3:19]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 73277ChloropyrazineHCID 58292699HCID 58292699, compound

Product 1

HCID 58292770HCID 58292770, compoundYield 81.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of ethyl 2-(1,6-dihydroxy-4-methoxy-1,3-dihydrobenzo[c][1,2]oxaborol-3-yl)acetate (0.15 g, 0.56 mmol), cesium carbonate (0.37 g, 1.12 mmol) and 2-chloropyrazine (96 mg, 0.84 mmol) in DMF (2 mL) was heated to 90° C. for 3 hr. The reaction mixture was quenched by saturated aqueous NaHCO3 (20 mL) and extracted with EtOAc (15 mL×2). The combined extracts were dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was purified by column chromatography (EtOAc/PE=1/2) on silica gel to give the title compound as a light yellow solid (156 mg, Y: 81.2%). MS (ESI) m/z=345 [M+H]+.

Workup

  1. customThe reaction mixture was quenched by saturated aqueous NaHCO3 (20 mL)
  2. extractionextracted with EtOAc (15 mL×2)
  3. dry with materialThe combined extracts were dried over anhydrous Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by column chromatography (EtOAc/PE=1/2) on silica gel

Sources & evidence

ORD record
ord-bb8415805f6e4141aafaf120984fa354
Source dataset
uspto-grants-2013_01
Patent number
US08343944B2

Reaction notes

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