Ethyl bromopyruvate → HCID 44125211, compound

HRID 2363756Notes

Reaction equation

HRID 2363756 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([B:8]2[O:12][C:11]([CH3:14])([CH3:13])[C:10]([CH3:16])([CH3:15])[O:9]2)=[CH:4][N:3]=1.[Br:17][CH2:18][C:19](=O)[C:20]([O:22][CH2:23][CH3:24])=[O:21]>COCCOC.C(OCC)C>[BrH:17].[CH3:15][C:10]1([CH3:16])[C:11]([CH3:14])([CH3:13])[O:12][B:8]([C:5]2[CH:6]=[CH:7][C:2]3[N:3]([CH:18]=[C:19]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[N:1]=3)[CH:4]=2)[O:9]1

Participants

5

Reactant 2

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

Product 1

HCID 44125211HCID 44125211, compoundYield 52.4%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
20 °C

Procedure

To a solution of 4 g of 2-amino-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine in 40 mL of 1,2-dimethoxyethane are added 4.26 g of ethyl 3-bromo-2-oxopropionate. The reaction mixture is stirred for 40 hours at 20° C. The precipitate is filtered off by suction, washed with a small amount of 1,2-dimethoxyethane and pentane and then taken up in 50 mL of ethanol and refluxed for 1 hour. The reaction mixture is concentrated to dryness under reduced pressure. The oil obtained is redissolved in ethyl ether and the solution is concentrated under reduced pressure. The solid is filtered off by suction and washed with a small amount of ethyl ether to give 3.78 g of ethyl 6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)imidazo[1,2-a]pyridine-2-carboxylate hydrobromide (1:1) in the form of a white solid.

Workup

  1. filtrationThe precipitate is filtered off by suction
  2. washwashed with a small amount of 1,2-dimethoxyethane and pentane
  3. temperaturerefluxed for 1 hour
  4. concentrationThe reaction mixture is concentrated to dryness under reduced pressure
  5. customThe oil obtained
  6. concentrationthe solution is concentrated under reduced pressure
  7. filtrationThe solid is filtered off by suction
  8. washwashed with a small amount of ethyl ether

Sources & evidence

ORD record
ord-ccdc045abc264183b31666397f7c5329
Source dataset
uspto-grants-2014_04
Patent number
US08691990B2

Reaction notes

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