Water → HCID 58292591, compound

HRID 1798166Notes

Reaction equation

HRID 1798166 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]([CH3:16])[C:7]1=2)[CH3:2].Cl[C:20]1[CH:25]=[C:24]([N+:26]([O-])=O)[CH:23]=[CH:22][N+:21]=1[O-].C([O-])([O-])=O.[Cs+].[Cs+].O>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:20]3[CH:25]=[C:24]([NH2:26])[CH:23]=[CH:22][N:21]=3)[CH:14]=[C:15]([CH3:16])[C:7]1=2)[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 844332-Chloro-4-nitropyridine 1-oxideHCID 58292549Ethyl 2-(1,6-dihydroxy-4-methyl-1,3-dihydrobenzo[c][1,2]oxaborol-3-yl)acetate

Product 1

HCID 58292591HCID 58292591, compoundYield 29%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(1,6-dihydroxy-4-methyl-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl)-acetic acid ethyl ester (2 g, 8 mmol), 2-chloro-4-nitro-pyridine oxide (2.2 g, 12 mmol) and Cs2CO3 (5.7 g, 18 mmol) were mixed in DMF (50 mL) and stirred at room temperature for 1 h. Water was added and the reaction mixture was adjusted to pH 3. The reaction mixture was extracted with ethyl acetate. The organic layers were concentrated to give a residue. The residue was purified by flash column chromatography (dichloromethane:methanol=15:1) to give the title compound (0.77 g, 29%) as a brown solid. MS found (electrospray): (M+H)+=389.1.

Workup

  1. extractionThe reaction mixture was extracted with ethyl acetate
  2. concentrationThe organic layers were concentrated
  3. customto give a residue
  4. customThe residue was purified by flash column chromatography (dichloromethane:methanol=15:1)

Sources & evidence

ORD record
ord-dff1f47aad6344ce84df5e44fb5e0920
Source dataset
uspto-grants-2013_01
Patent number
US08343944B2

Reaction notes

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