Cesium fluoride → HCID 66616139, compound

HRID 2172139Notes

Reaction equation

HRID 2172139 reaction equation
C([Si](C(C)C)(C(C)C)[N:5]1[CH:9]=[CH:8][C:7](B(O)O)=[CH:6]1)(C)C.I[C:20]1[CH:29]=[CH:28][C:23]([C:24]([O:26][CH3:27])=[O:25])=[CH:22][CH:21]=1.[F-].[Cs+]>C(COC)OC.O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[NH:5]1[CH:9]=[CH:8][C:7]([C:20]2[CH:29]=[CH:28][C:23]([C:24]([O:26][CH3:27])=[O:25])=[CH:22][CH:21]=2)=[CH:6]1

Participants

7

Reactant 3

HCID 25953Cesium fluorideHCID 69273Methyl 4-iodobenzoateHCID 27633031-(Triisopropylsilyl)pyrrole-3-boronic acid

Product 1

HCID 66616139HCID 66616139, compoundYield 58%

Reagents, catalysts & solvents 3

HCID 178418476HCID 178418476, compoundCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

To a solution of 1-(triisopropylsilyl)pyrrole-3-boronic acid (prepared according to the method of Alvarez, A.; Guzman, A.; Ruiz, A.; Velarde, E., J. Org. Chem. 1992, 57, 1653-1656) (6.12 g, 22.9 mmol) in anhydrous dimethoxyethane (76 mL) is added methyl 4-iodobenzoate (96.61 g, 25.2 mmol), dichlorobis(triphenylphosphine)palladium(II) (0.484 g, 0.69 mmol) and cesium fluoride (6.96 g, 45.8 mmol). The mixture is heated at reflux under a nitrogen atmosphere for 17 h. The reaction mixture is cooled to room temperature, diluted with water (100 mL) and extracted with ethyl acetate (4×25 mL). The extract is washed with water, dried over MgSO4 and concentrated to give the crude product. The product is purified by silica gel chromatography (5-15% ethyl acetate/hexane) to give 2.69 g of methyl 4-(1H-pyrrol-3-yl)-benzoate as a white solid (58% yield). 1H NMR (300 MHz, DMSO-d6): δ 3.83 (s, 3H), 6.53 (m, 1H), 6.83 (m, 1H), 7.35 (m, 1H), 7.66 (d, 2H, J=8.4 Hz), 7.86 (d, 2H, J=8.4 Hz), 11.11 (br s, 1H).

Workup

  1. temperatureThe mixture is heated
  2. temperatureat reflux under a nitrogen atmosphere for 17 h
  3. extractionextracted with ethyl acetate (4×25 mL)
  4. washThe extract is washed with water
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated
  7. customto give the crude product
  8. customThe product is purified by silica gel chromatography (5-15% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-e5f559e42e314b93b0b2e67939f8ef5d
Source dataset
uspto-grants-2015_06
Patent number
US09051342B2

Reaction notes

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