Cesium carbonate → Ethyl 2-(6-(6-chloropyridin-2-yloxy)-1-hydroxy-4-methyl-1,3-dihydrobenzo[c][1,2]oxaborol-3-yl)acetate

HRID 1798168Notes

Reaction equation

HRID 1798168 reaction equation
[OH:1][B:2]1[C:6]2[CH:7]=[C:8]([OH:12])[CH:9]=[C:10]([CH3:11])[C:5]=2[CH:4]([CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])[O:3]1.[Cl:19][C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([N+]([O-])=O)[N:21]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[Cl:19][C:20]1[N:21]=[C:22]([O:12][C:8]2[CH:9]=[C:10]([CH3:11])[C:5]3[CH:4]([CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])[O:3][B:2]([OH:1])[C:6]=3[CH:7]=2)[CH:23]=[CH:24][CH:25]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 27628862-Chloro-6-nitropyridineHCID 58292549Ethyl 2-(1,6-dihydroxy-4-methyl-1,3-dihydrobenzo[c][1,2]oxaborol-3-yl)acetate

Product 1

HCID 58292557Ethyl 2-(6-(6-chloropyridin-2-yloxy)-1-hydroxy-4-methyl-1,3-dihydrobenzo[c][1,2]oxaborol-3-yl)acetate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of ethyl 2-(1,6-dihydroxy-4-methyl-1,3-dihydrobenzo[c][1,2]oxaborol-3-yl)acetate (0.1 g, 0.4 mmol, 1 eq.) and 2-chloro-6-nitropyridine (158 mg, 1 mmol, 2.5 eq.) in 5 ml DMF was added cesium carbonate (392 mg, 1.2 mmol, 3 eq.). The reaction was stirred at room temperature for three hours. It was then quenched by water, extracted with EtOAc, washed with brine, dried over Na2SO4, and concentrated under reduced pressure. The crude was purified by column chromatography on silica gel (DCM/methanol=39:1 to 19:1) to give desired product as light yellow oil. MS (ESI) m/z=362 [M+H]+.

Workup

  1. customIt was then quenched by water
  2. extractionextracted with EtOAc
  3. washwashed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. customThe crude was purified by column chromatography on silica gel (DCM/methanol=39:1 to 19:1)

Sources & evidence

ORD record
ord-f5d64c5fc5204b9fbc4c3fd71559f424
Source dataset
uspto-grants-2013_01
Patent number
US08343944B2

Reaction notes

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