Ethyl Acetate → HCID 58875642, compound

HRID 1907780Notes

Reaction equation

HRID 1907780 reaction equation
Cl[C:2]1=[N:3][C:4]2[CH:16]=[CH:15][CH:14]=[CH:13][C:5]=2[O:6][C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]1=2.[CH3:17][O:18][C:19]([C:21]1[CH:26]=[CH:25][C:24](B(O)O)=[CH:23][CH:22]=1)=[O:20].C([O-])([O-])=O.[Na+].[Na+].CCOC(C)=O>COCCOC.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH:9]1[C:8]2[C:2]([C:24]3[CH:25]=[CH:26][C:21]([C:19]([O:18][CH3:17])=[O:20])=[CH:22][CH:23]=3)=[N:3][C:4]3[CH:16]=[CH:15][CH:14]=[CH:13][C:5]=3[O:6][C:7]=2[CH:12]=[CH:11][CH:10]=1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 10340Sodium CarbonateHCID 27343694-Methoxycarbonylphenylboronic acidHCID 706187211-Chlorodibenzo[b,f][1,4]oxazepine

Product 1

HCID 58875642HCID 58875642, compoundYield 99.3%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 554 (229 mg, 1.00 mmol) in DME (3 mL) was added 4-methoxycarbonylphenylboronic acid (216 mg, 1.20 mmol), Pd(PPh3)4 (0.065 mg, 0.056 mmol) and 2 N Na2CO3(aq) (1.5 mL, 3.0 mmol). The reaction mixture was stirred for 2 h at 90° C. The solution was then cooled at room temperature and poured into AcOEt. The organic layer was washed with water, brine and dried (Na2SO4), filtered and concentrated to give a yellow oil. The residue was purified by silica gel column chromatography with EtOAc (15%) in hexanes to afford 555 (327 mg, 99%) as a yellow foam. LRMS (ESI): (calc) 329.1 (found) 330.3 (MH)+.

Workup

  1. temperatureThe solution was then cooled at room temperature
  2. washThe organic layer was washed with water, brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give a yellow oil
  7. customThe residue was purified by silica gel column chromatography with EtOAc (15%) in hexanes

Sources & evidence

ORD record
ord-4d507503fa6f4181be0486a37399e6db
Source dataset
uspto-grants-2013_12
Patent number
US08598168B2

Reaction notes

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