1,2-Dimethoxyethane → HCID 66990168, compound

HRID 454705Notes

Reaction equation

HRID 454705 reaction equation
COCCOC.[O:7]1[CH:11]=[CH:10][CH:9]=[C:8]1B(O)O.C(=O)([O-])[O-].[Na+].[Na+].[CH2:21]([O:28][C:29]1[CH:51]=[CH:50][C:49]([N:52]2[CH2:57][CH2:56][O:55][CH2:54][CH2:53]2)=[CH:48][C:30]=1[C:31]([NH:33][C:34]1[CH:46]=[C:45](Br)[CH:44]=[CH:43][C:35]=1[C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])=[O:32])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>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(OCC)(=O)C.O>[CH2:21]([O:28][C:29]1[CH:51]=[CH:50][C:49]([N:52]2[CH2:53][CH2:54][O:55][CH2:56][CH2:57]2)=[CH:48][C:30]=1[C:31]([NH:33][C:34]1[CH:46]=[C:45]([C:8]2[O:7][CH:11]=[CH:10][CH:9]=2)[CH:44]=[CH:43][C:35]=1[C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])=[O:32])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

8

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 10340Sodium CarbonateHCID 2734357Furan-2-boronic acidHCID 66990199HCID 66990199, compound

Product 1

HCID 66990168HCID 66990168, compoundYield 71.6%

Reagents, catalysts & solvents 3

HCID 178418476HCID 178418476, compoundCatalyst2×HCID 962WaterSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
75 °C

Procedure

Ethylene glycol dimethyl ether (2.0 mL), water (0.60 mL), furan-2-boronic acid (0.047 g), sodium carbonate (0.093 g), and bis(triphenylphosphine)palladium(II) dichloride (4.9 mg) were added to tert-butyl 2-(2-(benzyloxy)-5-(morpholin-4-yl)benzamido)-4-bromobenzoate (0.20 g), followed by stirring at 75° C. for 2 hours. The reaction mixture was cooled to room temperature, and bis(triphenylphosphine)palladium(II) dichloride (4.9 mg) was added thereto, followed by stirring at 75° C. for 2 hours. The reaction mixture was cooled to room temperature, and water and ethyl acetate were added thereto. The organic layer was separated and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography [eluent: 85-70% hexane/ethyl acetate] to obtain 0.14 g of tert-butyl 2-(2-(benzyloxy)-5-(morpholin-4-yl)benzamido)-4-(furan-2-yl)benzoate as a light yellow solid.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. stirringby stirring at 75° C. for 2 hours
  3. temperatureThe reaction mixture was cooled to room temperature
  4. customThe organic layer was separated
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. customThe obtained residue was purified by silica gel column chromatography [eluent: 85-70% hexane/ethyl acetate]

Sources & evidence

ORD record
ord-7542821ee02a49ca98bc462deef457bf
Source dataset
uspto-grants-2013_07
Patent number
US08492582B2

Reaction notes

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