Cesium carbonate → HCID 58292774, compound

HRID 1798124Notes

Reaction equation

HRID 1798124 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.C([O-])([O-])=O.[Cs+].[Cs+].Cl.Cl[CH2:27][CH2:28][N:29]([CH3:31])[CH3:30]>CN(C=O)C>[CH3:30][N:29]([CH3:31])[CH2:28][CH2:27][O:12][C:8]1[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][B:2]([OH:1])[C:6]=2[CH:7]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 11636816N,N-Dimethylaminoethyl chloride hydrochlorideHCID 58292549Ethyl 2-(1,6-dihydroxy-4-methyl-1,3-dihydrobenzo[c][1,2]oxaborol-3-yl)acetate

Product 1

HCID 58292774HCID 58292774, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

To the mixture of ethyl 2-(1,6-dihydroxy-4-methyl-1,3-dihydrobenzo[c][1,2]oxaborol-3-yl)acetate (200 mg, 0.8 mmol) in 15 ml DMF was added Cs2CO3 (782 mg, 2.4 mmol), followed by 2-chloro-N,N-dimethylethanamine hydrochloride (116 mg, 0.81 mmol). The mixture was heated to 90° C. for 6 h and quenched by ice water (20 mL). The resulting mixture was extracted with EtOAc (3×20 ml) and the combined organic layers were dried over anhydrous Na2SO4 and concentrated to dryness. The residue was used directly in next step reaction without further purification.

Workup

  1. customquenched by ice water (20 mL)
  2. extractionThe resulting mixture was extracted with EtOAc (3×20 ml)
  3. dry with materialthe combined organic layers were dried over anhydrous Na2SO4
  4. concentrationconcentrated to dryness
  5. customThe residue was used directly in next step reaction without further purification

Sources & evidence

ORD record
ord-bcdf4ed21d3947b3993a0cfd08476426
Source dataset
uspto-grants-2013_01
Patent number
US08343944B2

Reaction notes

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