Potassium Phosphate, Tribasic → HCID 68507568, compound

HRID 1990896Notes

Reaction equation

HRID 1990896 reaction equation
[CH2:1]([O:3][C:4](=[O:15])[C:5]1[CH:10]=[CH:9][C:8](I)=[C:7]([O:12][CH2:13][CH3:14])[CH:6]=1)[CH3:2].[F:16][C:17]1[CH:22]=[CH:21][C:20](B(O)O)=[CH:19][CH:18]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>CN(C=O)C.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH2:1]([O:3][C:4]([C:5]1[CH:10]=[CH:9][C:8]([C:20]2[CH:21]=[CH:22][C:17]([F:16])=[CH:18][CH:19]=2)=[C:7]([O:12][CH2:13][CH3:14])[CH:6]=1)=[O:15])[CH3:2]

Participants

6

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 2856454-Fluorophenylboronic acidHCID 23090718Ethyl 3-ethoxy-4-iodobenzoate

Product 1

HCID 68507568HCID 68507568, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 3-ethoxy-4-iodo-benzoic acid ethyl ester (0.76 g, 2.37 mmol, 1.0 equiv; [CAS RN 741699-04-7], prepared according to WO 04/072 016 A1 (Kissei Pharmaceuticals Co, Ltd.)) in anhydrous DMF (12 mL) under Ar was added 4-fluorophenyl boronic acid (0.40 g, 2.85 mmol, 1.2 equiv), K3PO4 (0.86 g, 4.04 mmol, 1.7 equiv) and tetrakis(triphenylphosphine) palladium(0) (82.3 mg, 0.071 mmol, 0.03 equiv) and the reaction mixture stirred at 80° C. for 16 h. The reaction mixture was poured on ice, extracted with ethyl acetate (2×100 mL) and the combined organic phases washed with water (2×100 mL). The organic phase was dried over MgSO4, concentrated by evaporation under reduced pressure and the crude reaction product purified with column chromatography on silica eluting with hexane/ethyl acetate (95:5) to give 0.51 g (75%) of the title compound.

Workup

  1. additionThe reaction mixture was poured on ice
  2. extractionextracted with ethyl acetate (2×100 mL)
  3. washthe combined organic phases washed with water (2×100 mL)
  4. dry with materialThe organic phase was dried over MgSO4
  5. concentrationconcentrated by evaporation under reduced pressure
  6. customthe crude reaction product
  7. custompurified with column chromatography on silica eluting with hexane/ethyl acetate (95:5)

Sources & evidence

ORD record
ord-5b2e4a4a60404dafb70e6dd6357b4b51
Source dataset
uspto-grants-2010_01
Patent number
US07645753B2

Reaction notes

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