Ethanol → HCID 44125210, compound

HRID 1878505Notes

Reaction equation

HRID 1878505 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([B:8]2[O:12]C(C)(C)C(C)(C)[O:9]2)=[CH:4][N:3]=1.Br[CH2:18][C:19](=O)[C:20]([O:22][CH2:23][CH3:24])=[O:21].C(O)C>COCCOC>[CH2:23]([O:22][C:20]([C:19]1[N:1]=[C:2]2[CH:7]=[CH:6][C:5]([B:8]([OH:9])[OH:12])=[CH:4][N:3]2[CH:18]=1)=[O:21])[CH3:24]

Participants

5

Reactant 3

HCID 702EthanolHCID 66144Ethyl bromopyruvateHCID 27565555-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amine

Product 1

HCID 44125210HCID 44125210, compound

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of 2.5 g of 2-amino-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine in 50 mL of 1,2-dimethoxyethane are added 2.14 mL of ethyl 3-bromo-2-oxopropionate. The reaction mixture is stirred for 3.5 hours at 25° C., 50 mL of ethanol are then added and the resulting mixture is refluxed for 16 hours. The reaction mixture is cooled and concentrated to dryness. The residue is suspended in 100 mL of water at 0° C. and treated, while stirring vigorously, with solid sodium carbonate until a pH of 8-9 is obtained. The precipitate is filtered off by suction and washed with 100 mL of water at 0° C. and then dissolved in 150 mL of methanol. The solution is dried over magnesium sulfate, filtered, concentrated and dried under vacuum to give 2.36 g of 2-ethoxycarbonylimidazo[1,2-a]pyridine-6-boronic acid in the form of a cream-coloured solid.

Workup

  1. temperaturethe resulting mixture is refluxed for 16 hours
  2. temperatureThe reaction mixture is cooled
  3. concentrationconcentrated to dryness
  4. customis suspended in 100 mL of water at 0° C.
  5. additiontreated
  6. stirringwhile stirring vigorously, with solid sodium carbonate until a pH of 8-9
  7. customis obtained
  8. filtrationThe precipitate is filtered off by suction
  9. washwashed with 100 mL of water at 0° C.
  10. dissolutiondissolved in 150 mL of methanol
  11. dry with materialThe solution is dried over magnesium sulfate
  12. filtrationfiltered
  13. concentrationconcentrated
  14. customdried under vacuum

Sources & evidence

ORD record
ord-c420bf6ac2104e439c5c531507050dc3
Source dataset
uspto-grants-2012_11
Patent number
US08314109B2

Reaction notes

Loading…