1,2-Dimethoxyethane → HCID 69253381, compound

HRID 2224620Notes

Reaction equation

HRID 2224620 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([N:12]([CH2:22][O:23][CH2:24][CH2:25][Si:26]([CH3:29])([CH3:28])[CH3:27])[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2B(O)O)(=[O:11])=[O:10])=[CH:5][CH:4]=1.Br[C:31]1[CH:36]=[CH:35][C:34]([F:37])=[CH:33][C:32]=1C(=O)C.C(=O)([O-])[O-].[Na+].[Na+].[CH2:47]([CH2:50][O:51]C)OC>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>[C:50]([C:31]1[CH:36]=[CH:35][C:34]([F:37])=[CH:33][C:32]=1[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=1[N:12]([CH2:22][O:23][CH2:24][CH2:25][Si:26]([CH3:29])([CH3:28])[CH3:27])[S:9]([C:6]1[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1)(=[O:11])=[O:10])(=[O:51])[CH3:47]

Participants

7

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 10340Sodium CarbonateHCID 227360801-(2-Bromo-5-fluorophenyl)ethan-1-oneHCID 69255310HCID 69255310, compound

Product 1

HCID 69253381HCID 69253381, compound

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 702EthanolSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 2-([(4-methoxyphenyl)sulfonyl]{[2-(trimethylsilyl)ethoxy]methyl}amino) phenylboronic acid (3.31 g, 7.57 mmol) and tetrakis(triphenylphosphine) palladium (0) (0.87 g, 0.76 mmol) in dimethoxyethane (30 niL) under argon was added 1-(2-bromo-5-fluorophenyl)ethanone (1.86 g, 8.57 mmol) in ethanol (1 mL). Aqueous sodium carbonate (2 M, 40 mL) was added and the reaction mixture was heated at 90° C. for 14 hours. The solvent was removed in vacuo and the residue was partitioned between water and ethyl acetate. The organic layer was washed with water and a saturated, aqueous sodium chloride solution. After drying over anhydrous magnesium sulfate, the organic phase was filtered and the filtrate was evaporated in vacuo to yield the crude title compound as an oil. Purification by silica gel column chromatography by elution with hexane-ethyl acetate (5:1) gave the title compound as a pale yellow oil, which crystallized on standing (2.22 g, 4.19 mmol, 55 %), m.p. 94-95° C.

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue was partitioned between water and ethyl acetate
  3. washThe organic layer was washed with water
  4. dry with materialAfter drying over anhydrous magnesium sulfate
  5. filtrationthe organic phase was filtered
  6. customthe filtrate was evaporated in vacuo
  7. customto yield the crude title compound as an oil
  8. customPurification by silica gel column chromatography
  9. washby elution with hexane-ethyl acetate (5:1)

Sources & evidence

ORD record
ord-d015fbda94a9499a90fa2ad9172e2ac4
Source dataset
uspto-grants-2008_05
Patent number
US07378427B2

Reaction notes

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