Toluene → Ethyl 2-(4-(2-bromopyridin-4-yl)phenyl)acetate

HRID 592227Notes

Reaction equation

HRID 592227 reaction equation
[Br:1][C:2]1[CH:7]=[C:6](I)[CH:5]=[CH:4][N:3]=1.CC1(C)C(C)(C)OB([C:17]2[CH:22]=[CH:21][C:20]([CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])=[CH:19][CH:18]=2)O1.C([O-])([O-])=O.[Na+].[Na+].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.C(O)C.O>[Br:1][C:2]1[CH:7]=[C:6]([C:17]2[CH:22]=[CH:21][C:20]([CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])=[CH:19][CH:18]=2)[CH:5]=[CH:4][N:3]=1

Participants

8

Reactant 4

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 10515202-Bromo-4-iodopyridineHCID 46737998Ethyl (4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetate

Product 1

HCID 58447951Ethyl 2-(4-(2-bromopyridin-4-yl)phenyl)acetate

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

To a sealed tube were added 2-bromo-4-iodopyridine 203-1 (568 mg, 2.0 mmol), ethyl 2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetate 203-2 (580 mg, 2.0 mmol), Pd(PPh3)4 (116 mg, 0.1 mmol), Na2CO3 (636 mg, 6.0 mmol), toluene (4 mL), H2O (4 mL) and ethanol (1 mL). The reaction mixture was bubbled with nitrogen for 2 minutes and stirred at 80° C. for 10 hours. After cooling to room temperature, the solvents were evaporated and the residue was redissolved in water (5 ml) and extracted with ethyl acetate (5 mL×3). The combined organic phases were dried over Na2SO4, and concentrated. The residue was purified by silica gel flash chromatography and eluted with 15% ethyl acetate in hexane to give ethyl 2-(4-(2-bromopyridin-4-yl)phenyl)acetate 203-3. MS m/z 320.1 (M+1).

Workup

  1. customThe reaction mixture was bubbled with nitrogen for 2 minutes
  2. temperatureAfter cooling to room temperature
  3. customthe solvents were evaporated
  4. dissolutionthe residue was redissolved in water (5 ml)
  5. extractionextracted with ethyl acetate (5 mL×3)
  6. dry with materialThe combined organic phases were dried over Na2SO4
  7. concentrationconcentrated
  8. customThe residue was purified by silica gel flash chromatography
  9. washeluted with 15% ethyl acetate in hexane

Sources & evidence

ORD record
ord-da6cb89535d64ad78bb1f216dc2c1f44
Source dataset
uspto-grants-2016_01
Patent number
US09238646B2

Reaction notes

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