Potassium Carbonate → HCID 21914168, compound

HRID 1632108Notes

Reaction equation

HRID 1632108 reaction equation
I[C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[O:11][CH3:12].[Cl:13][C:14]1[CH:15]=[C:16](B(O)O)[CH:17]=[CH:18][CH:19]=1.C(=O)([O-])[O-].[K+].[K+].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.CCO.O1CCOCC1>[Cl:13][C:14]1[CH:19]=[C:18]([C:2]2[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=2[O:11][CH3:12])[CH:17]=[CH:16][CH:15]=1

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 11776TriphenylphosphineHCID 948062-Iodo-1-methoxy-4-nitrobenzeneHCID 2734323(3-Chlorophenyl)boronic acid

Product 1

HCID 21914168HCID 21914168, compoundYield 64%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 702EthanolSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

In a 3-neck 500 mL round bottomed flask equipped with a stir bar, condenser and nitrogen lines was placed was placed 2-iodo-1-methoxy-4-nitrobenzene (7.0 g, 25.1 mmol), 3-chlorophenylboronic acid (4.32 g, 27.6 mmol), potassium carbonate (10.4 g, 75.3 mmol), triphenylphosphine (1.98 g, 7.53 mmol), 1,4-dioxane (50 mL), 50% aqueous EtOH followed by palladium acetate (564 mg, 2.51 mmol). The mixture was heated to 90° C. in an oil bath for 16 hours and then quenched with 1M aqueous HCl (80 mL). After the reaction mixture was filtered through Celite, water (100 mL) and 1M aqueous HCl (100 mL) were added followed by extractions with ethyl acetate (3×150 mL). The organic portions were combined, washed with brine (250 mL), dried (MgSO4) and concentrated. The residue was purified by column utilizing 20% EtOAc/Hexanes as the eluent to produce 4.26 g of I-256 as an orange solid in 64% yield. MS (ESI+): 263.3 (M+).

Workup

  1. customIn a 3-neck 500 mL round bottomed flask equipped with a stir bar, condenser
  2. customquenched with 1M aqueous HCl (80 mL)
  3. filtrationAfter the reaction mixture was filtered through Celite, water (100 mL) and 1M aqueous HCl (100 mL)
  4. additionwere added
  5. extractionfollowed by extractions with ethyl acetate (3×150 mL)
  6. washwashed with brine (250 mL)
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated
  9. customThe residue was purified by column utilizing 20% EtOAc/Hexanes as the eluent
  10. customto produce 4.26 g of I-256 as an orange solid in 64% yield

Sources & evidence

ORD record
ord-d83c20f7adfc44128280d51a824b3e14
Source dataset
uspto-grants-2014_07
Patent number
US08791267B2

Reaction notes

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