Water → HCID 59192524, compound

HRID 2384007Notes

Reaction equation

HRID 2384007 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([Cl:8])=[N:6][CH:7]=1.[CH:9]([C:12]1[CH:13]=[C:14](B(O)O)[CH:15]=[CH:16][CH:17]=1)([CH3:11])[CH3:10].O.C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1.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>[Cl:8][C:5]1[CH:4]=[CH:3][C:2]([C:16]2[CH:15]=[CH:14][CH:13]=[C:12]([CH:9]([CH3:11])[CH3:10])[CH:17]=2)=[CH:7][N:6]=1

Participants

7

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 27344145-Bromo-2-chloropyridineHCID 27734783-Isopropylbenzeneboronic acid

Product 1

HCID 59192524HCID 59192524, compoundYield 59%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

To a stirred solution of 5-bromo-2-chloropyridine (1.27 g, 6.63 mmol) in toluene (30 mL) was added an ethanolic solution (10 mL) of 3-isopropyl-phenylboronic acid (1.8 g, 11.28 mmol) followed by water (10 mL) and potassium carbonate (2.76 g, 20.0 mmol). The resulting mixture was degassed for 15 min (by purging with argon). At this time, Pd(PPh3)4 (0.613 g, 0.53 mmol) was added under argon and the reaction mixture was heated at 80° C. for 4 h. The reaction mixture was then cooled to room temperature and extracted with ethyl acetate (3×10 mL). The combined organic layers were washed with water (2×10 mL), dried over Na2SO4 and concentrated in vacuo to obtain the crude product, which was purified over silica gel (Biotage column chromatography, 2% ethyl acetate in hexane) to afford 0.900 g (59%) of 2-chloro-5-(3-isopropyl-phenyl)-pyridine.

Workup

  1. customThe resulting mixture was degassed for 15 min
  2. custom(by purging with argon)
  3. temperatureThe reaction mixture was then cooled to room temperature
  4. extractionextracted with ethyl acetate (3×10 mL)
  5. washThe combined organic layers were washed with water (2×10 mL)
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated in vacuo
  8. customto obtain the crude product, which
  9. customwas purified over silica gel (Biotage column chromatography, 2% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-0acc0025e9e5431c82941bc424266945
Source dataset
uspto-grants-2012_09
Patent number
US08263656B2

Reaction notes

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