Cesium carbonate → Ethyl 2-(6-(5-cyanothiazol-2-yloxy)-1-hydroxy-4-methyl-1,3-dihydrobenzo[c][1,2]oxaborol-3-yl)acetate

HRID 1798278Notes

Reaction equation

HRID 1798278 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[C:20]1[S:21][C:22]([C:25]#[N:26])=[CH:23][N:24]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[C:25]([C:22]1[S:21][C:20]([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)=[N:24][CH:23]=1)#[N:26]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 14852222-Chlorothiazole-5-carbonitrileHCID 58292549Ethyl 2-(1,6-dihydroxy-4-methyl-1,3-dihydrobenzo[c][1,2]oxaborol-3-yl)acetate

Product 1

HCID 67253421Ethyl 2-(6-(5-cyanothiazol-2-yloxy)-1-hydroxy-4-methyl-1,3-dihydrobenzo[c][1,2]oxaborol-3-yl)acetateYield 80%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

To a mixture of ethyl 2-(1,6-dihydroxy-4-methyl-1,3-dihydrobenzo[c][1,2]oxaborol-3-yl)acetate (3.75 g, 15 mmol, 1 eq.) and 2-chlorothiazole-5-carbonitrile (3.25 g, 22.5 mmol, 1.5 eq.) in 100 ml DMF was added cesium carbonate (14 g, 45 mmol, 3 eq.). The reaction was heated at 70° C. for two 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 (4.3 g, yield 80%). MS (ESI) m/z=717 [2M+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 (4.3 g, yield 80%)

Sources & evidence

ORD record
ord-2678b580c87f4c15bd102bd7b6462d8b
Source dataset
uspto-grants-2013_01
Patent number
US08343944B2

Reaction notes

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