Potassium Fluoride → HCID 68690453, compound

HRID 1159068Notes

Reaction equation

HRID 1159068 reaction equation
[CH2:1]([N:3]([CH2:15][CH3:16])[C:4](=[O:14])[C:5]1[CH:10]=[CH:9][C:8](Cl)=[CH:7][C:6]=1[O:12][CH3:13])[CH3:2].[F-].[K+].B1(C=C)OB([CH:25]=[CH2:26])OB(C=C)O1.C1C=CN=CC=1>O1CCOCC1.[Cl-].[Na+].O.CC(C)([P](C(C)(C)C)([Pd][P](C(C)(C)C)(C(C)(C)C)C(C)(C)C)C(C)(C)C)C>[CH2:1]([N:3]([CH2:15][CH3:16])[C:4](=[O:14])[C:5]1[CH:10]=[CH:9][C:8]([CH:25]=[CH2:26])=[CH:7][C:6]=1[O:12][CH3:13])[CH3:2]

Participants

7

Reactant 3

HCID 522689Potassium FluorideHCID 27348062,4,6-Trivinylboroxin-Pyridine ComplexHCID 61947154HCID 61947154, compound

Product 1

HCID 68690453HCID 68690453, compoundYield 49%

Reagents, catalysts & solvents 3

HCID 178418851HCID 178418851, compoundCatalystHCID 312751,4-DioxaneSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a stirring degassed solution of N,N-diethyl-4-chloro-2-methoxybenzamide (65 mg, 0.35 mmol), potassium fluoride (134 mg, 2.3 mmol), and 2,4,6-trivinylcyclotriboroxane pyridine complex (132 mg, 0.35 mmol) in 1,4-dioxane (3 mL) was added bis(tri-t-butylphosphine)palladium (5 mg, 0.01 mmol). The reaction was heated to reflux for 5 h and then cooled to room temperature. The reaction was diluted with brine and extracted with EtOAc (3×5 mL). The organic layers were combined, dried over Na2SO4, and conc. in vacuo to a pale yellow oil. The oil was purified by flash chromatography (SiO2, 0-50% EtOAc in hexanes) to give 40 mg of the desired product as a colorless oil. MS (ESI) 234 (M+H).

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux for 5 h
  3. extractionextracted with EtOAc (3×5 mL)
  4. dry with materialdried over Na2SO4
  5. customThe oil was purified by flash chromatography (SiO2, 0-50% EtOAc in hexanes)

Sources & evidence

ORD record
ord-6c6b8c00db3344ceaf74f8fb77780f23
Source dataset
uspto-grants-2010_10
Patent number
US07812024B2

Reaction notes

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