1,2-Dimethoxyethane → HCID 57732421, compound

HRID 1365061Notes

Reaction equation

HRID 1365061 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5](I)=[CH:4][C:3]=1[C:9]([C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([N+:17]([O-:19])=[O:18])[CH:12]=1)=[O:10].[N:20]1[CH:25]=[CH:24][C:23](B(O)O)=[CH:22][CH:21]=1.C(COC)OC.C(=O)([O-])[O-].[Na+].[Na+]>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.C(O)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:23]2[CH:24]=[CH:25][N:20]=[CH:21][CH:22]=2)=[CH:4][C:3]=1[C:9]([C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([N+:17]([O-:19])=[O:18])[CH:12]=1)=[O:10]

Participants

7

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 10340Sodium CarbonateHCID 2734379(Pyridin-4-yl)boronic acidHCID 57732436HCID 57732436, compound

Product 1

HCID 57732421HCID 57732421, compoundYield 56.5%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 702EthanolSolvent

Procedure

A 20 mL microwave tube was charged with (2-fluoro-5-iodophenyl)(3-nitrophenyl)methanone (1.1 g), 4-pyridylboronic acid (730 mg), dichlorobis(triphenylphosphine)palladium(II) (420 mg), dimethoxyethane (8 mL), ethanol (4 mL) and a saturated solution of sodium carbonate (2 mL) then heated to 110° C. for 360 s using microwave irradiation. The reaction was concentrated to dryness and the residue was taken up in water then extracted with ethyl acetate. The organic extracts were combined and dried over magnesium sulfate. The drying salts were removed by filtration and the filtrate was concentrated. The residue was purified by silica gel chromatography to provide [2-fluoro-5-(4-pyridinyl)phenyl](3-nitrophenyl)methanone (540 mg) as a solid. H1 NMR (d6-dmso): 8.63 (d, 2H), 8.52 (dd, 1H), 8.48 (s, 1H), 8.21 (d, 1H), 8.15 (m, 1H), 8.06 (dd, 1H), 7.85 (dd, 1H), 7.74 (d, 2H), 7.58 (dd, 1H).

Workup

  1. custommicrowave irradiation
  2. concentrationThe reaction was concentrated to dryness
  3. extractionthen extracted with ethyl acetate
  4. dry with materialdried over magnesium sulfate
  5. customThe drying salts were removed by filtration
  6. concentrationthe filtrate was concentrated
  7. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-ff9728e0ac9242519e9894f3c77d641d
Source dataset
uspto-grants-2011_02
Patent number
US07888503B2

Reaction notes

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