Potassium Carbonate → HCID 87242613, compound

HRID 1051318Notes

Reaction equation

HRID 1051318 reaction equation
Br[C:2]1[N:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]2=[N:4][C:3]=1[C:11]1[CH:18]=[CH:17][C:14]([CH:15]=[O:16])=[CH:13][CH:12]=1.[F:19][C:20]1[CH:25]=[CH:24][C:23](B(O)O)=[CH:22][CH:21]=1.C([O-])([O-])=O.[K+].[K+].O.C(O)C>C1(C)C=CC=CC=1.O>[F:19][C:20]1[CH:25]=[CH:24][C:23]([C:2]2[N:6]3[CH:7]=[CH:8][CH:9]=[CH:10][C:5]3=[N:4][C:3]=2[C:11]2[CH:18]=[CH:17][C:14]([CH:15]=[O:16])=[CH:13][CH:12]=2)=[CH:22][CH:21]=1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 2856454-Fluorophenylboronic acidHCID 820986HCID 820986, compoundHCID 19096565Water ethanol

Product 1

HCID 87242613HCID 87242613, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
90 °C

Procedure

0.46 g (1.5 mM) 4-(3-bromoimidazo[1,2-a]pyridin-2-yl)benzaldehyde (prepared as described by Sundberg et al.; J. Heterocyclic Chem., 25, 129, 1988) is dissolved in 5 mL of toluene. To this mixture is added 4-fluorphenyl boronic acid (1.5 eq) followed by tetrakis triphenylphosphine palladium (0) 10% by wt, K2CO3 (3 eq) and ethanol water mixture (4 mL). The reaction mixture is heated at 90° C. for 4-6 h. The reaction is cooled to room temperature and 20 mL of water is added and the reaction mixture is extracted with ethyl acetate. The organic layer is dried and concentrated. The crude is purified by flash column chromatography to obtain the desired compound.

Workup

  1. temperatureThe reaction is cooled to room temperature
  2. extractionthe reaction mixture is extracted with ethyl acetate
  3. customThe organic layer is dried
  4. concentrationconcentrated
  5. customThe crude is purified by flash column chromatography

Sources & evidence

ORD record
ord-3d72e44f2b534187ab0bbfbb48d10424
Source dataset
uspto-grants-2016_07
Patent number
US09387204B2

Reaction notes

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