Cesium carbonate → HCID 86690474, compound

HRID 1026749Notes

Reaction equation

HRID 1026749 reaction equation
Br[C:2]1[CH:7]=[C:6]([CH2:8][NH:9][CH:10]([CH3:12])[CH3:11])[CH:5]=[CH:4][N:3]=1.[F:13][C:14]1[CH:19]=[CH:18][C:17](B(O)O)=[CH:16][CH:15]=1.C(=O)([O-])[O-].[Cs+].[Cs+].C(=O)([O-])O.[Na+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(OCC)(=O)C.O.C(O)C.C1(C)C=CC=CC=1>[F:13][C:14]1[CH:19]=[CH:18][C:17]([C:2]2[CH:7]=[C:6]([CH2:8][NH:9][CH:10]([CH3:12])[CH3:11])[CH:5]=[CH:4][N:3]=2)=[CH:16][CH:15]=1

Participants

10

Reactant 4

HCID 10796Cesium carbonateHCID 2856454-Fluorophenylboronic acidHCID 516892Sodium BicarbonateHCID 53385538N-[(2-Bromopyridin-4-yl)methyl]propan-2-amine

Product 1

HCID 86690474HCID 86690474, compoundYield 53%

Reagents, catalysts & solvents 5

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 962WaterSolventHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of N-[(2-bromopyridin-4-yl)methyl]propan-2-amine (2.00 g), 4-fluorophenylboronic acid (1.34 g), cesium carbonate (4.26 g), tetrakis(triphenylphosphine)palladium (1.01 g), toluene (4.5 mL), ethanol (4.5 mL) and water (3.0 mL) was stirred under irradiation with microwave while heating at 150° C. for 30 min. Saturated aqueous sodium hydrogen carbonate solution and ethyl acetate were added to the reaction mixture, and the resulting mixture was then filtered through Celite and extracted with ethyl acetate. The whole organic phase was collected and dried over magnesium sulfate. After the desiccant was filtered off, the solution was concentrated under reduced pressure. The resulting residue was purified by column chromatography (silica gel cartridge, chloroform:methanol=96:4-92:8) and (NH silica gel cartridge, hexane:ethyl acetate=90:10-60:40) to afford the title compound (1.13 g).

Workup

  1. filtrationthe resulting mixture was then filtered through Celite
  2. extractionextracted with ethyl acetate
  3. customThe whole organic phase was collected
  4. dry with materialdried over magnesium sulfate
  5. filtrationAfter the desiccant was filtered off
  6. concentrationthe solution was concentrated under reduced pressure
  7. customThe resulting residue was purified by column chromatography (silica gel cartridge, chloroform:methanol=96:4-92:8) and (NH silica gel cartridge, hexane:ethyl acetate=90:10-60:40)

Sources & evidence

ORD record
ord-e92c977e3fae4cef8c68e551f184cff5
Source dataset
uspto-grants-2014_05
Patent number
US08729271B2

Reaction notes

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