Cesium carbonate → HCID 58292807, compound

HRID 1798245Notes

Reaction equation

HRID 1798245 reaction equation
[CH2:1]([O:8][C:9]1[C:17]2[CH:16]([CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])[O:15][B:14]([OH:24])[C:13]=2[CH:12]=[C:11]([OH:25])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])([O-])=O.[Cs+].[Cs+].Cl[C:33]1[CH:38]=[N:37][CH:36]=[CH:35][N:34]=1>CN(C=O)C>[CH2:1]([O:8][C:9]1[C:17]2[CH:16]([CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])[O:15][B:14]([OH:24])[C:13]=2[CH:12]=[C:11]([O:25][C:33]2[CH:38]=[N:37][CH:36]=[CH:35][N:34]=2)[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 73277ChloropyrazineHCID 58292665HCID 58292665, compound

Product 1

HCID 58292807HCID 58292807, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

To a mixture of ethyl 2-(4-(benzyloxy)-1,6-dihydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-3-yl)acetate (1.00 g, 2.9 mmol) and anhydrous Cs2CO3 (1.12 g, 5.84 mmol) in DMF (10 mL) was added 2-chloropyrazine (0.40 g, 3.5 mmol). The reaction mixture was stirred at 90° C. for 1 h and quenched by addition of water (15 mL). The resulting mixture was extracted by EtOAc and the combined organic layers were washed with water (20 mL) and brine (25 mL), dried over anhydrous Na2SO4 and concentrated in vacuo to give the title compound as a yellow oil (0.74 g, Yield: 61%).

Workup

  1. customquenched by addition of water (15 mL)
  2. extractionThe resulting mixture was extracted by EtOAc
  3. washthe combined organic layers were washed with water (20 mL) and brine (25 mL)
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-25e5518d404f47f6afe6e431fbd9486d
Source dataset
uspto-grants-2013_01
Patent number
US08343944B2

Reaction notes

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