5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amine → N-phenyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)imidazo[1,2-a]pyridine-2-carboxamide hydrobromide

HRID 2363725Notes

Reaction equation

HRID 2363725 reaction equation
[Br:1][CH2:2][C:3](=O)[C:4]([NH:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:5].[NH2:14][C:15]1[CH:20]=[CH:19][C:18]([B:21]2[O:25][C:24]([CH3:27])([CH3:26])[C:23]([CH3:29])([CH3:28])[O:22]2)=[CH:17][N:16]=1>COCCOC>[BrH:1].[C:7]1([NH:6][C:4]([C:3]2[N:14]=[C:15]3[CH:20]=[CH:19][C:18]([B:21]4[O:25][C:24]([CH3:27])([CH3:26])[C:23]([CH3:29])([CH3:28])[O:22]4)=[CH:17][N:16]3[CH:2]=2)=[O:5])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

4

Reactant 2

HCID 27565555-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amineHCID 132915193-Bromo-2-oxo-N-phenylpropanamide

Product 1

HCID 68778296N-phenyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)imidazo[1,2-a]pyridine-2-carboxamide hydrobromideYield 51.1%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

1°) To a solution of 0.8 g of 3-bromo-2-oxo-N-phenylpropionamide in 30 mL of 1,2-dimethoxyethane is added 0.87 g of 2-amino-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine. The reaction mixture is stirred for 16 hours at room temperature and then concentrated to dryness under reduced pressure. The residue is taken up in 15 mL of ethanol and refluxed for 2 hours. After concentrating to dryness under reduced pressure, the residue is crystallized from ethanol, filtered off by suction and washed with ethanol and then with ethyl ether to give 0.75 g of N-phenyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)imidazo[1,2-a]pyridine-2-carboxamide hydrobromide (1:1) in the form of a white solid.

Workup

  1. concentrationconcentrated to dryness under reduced pressure
  2. temperaturerefluxed for 2 hours
  3. concentrationAfter concentrating to dryness under reduced pressure
  4. customthe residue is crystallized from ethanol
  5. filtrationfiltered off by suction
  6. washwashed with ethanol

Sources & evidence

ORD record
ord-514c2dcc09b144e19068c5268f590a31
Source dataset
uspto-grants-2014_04
Patent number
US08691990B2

Reaction notes

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