Sodium Carbonate → Tert-butyl 4-(3-(tert-butoxycarbonylamino)phenyl)-2-nitrobenzoate

HRID 454513Notes

Reaction equation

HRID 454513 reaction equation
C(=O)([O-])[O-].[Na+].[Na+].[C:7]([O:11][C:12]([NH:14][C:15]1[CH:16]=[C:17](B(O)O)[CH:18]=[CH:19][CH:20]=1)=[O:13])([CH3:10])([CH3:9])[CH3:8].Br[C:25]1[CH:37]=[CH:36][C:28]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])=[C:27]([N+:38]([O-:40])=[O:39])[CH:26]=1.C(=O)(O)[O-].[Na+]>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.C(OCC)(=O)C.COCCOC.O>[C:7]([O:11][C:12]([NH:14][C:15]1[CH:16]=[C:17]([C:25]2[CH:37]=[CH:36][C:28]([C:29]([O:31][C:32]([CH3:34])([CH3:35])[CH3:33])=[O:30])=[C:27]([N+:38]([O-:40])=[O:39])[CH:26]=2)[CH:18]=[CH:19][CH:20]=1)=[O:13])([CH3:10])([CH3:9])[CH3:8]

Participants

9

Reactant 4

HCID 10340Sodium CarbonateHCID 516892Sodium BicarbonateHCID 2773228(3-Boc-aminophenyl)boronic acidHCID 26369829tert-Butyl 4-bromo-2-nitrobenzoate

Product 1

HCID 66990036Tert-butyl 4-(3-(tert-butoxycarbonylamino)phenyl)-2-nitrobenzoateYield 82.6%

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Water (0.6 mL), sodium carbonate (0.16 g), 3-(tert-butoxycarbonylamino)phenylboronic acid (0.14 g), and tetrakis(triphenylphosphine)palladium(0) (29 mg) were added to an ethylene glycol dimethyl ether (2.0 mL) solution of tert-butyl 4-bromo-2-nitrobenzoate (0.15 g), followed by heating to reflux under a nitrogen atmosphere for 2 hours. The reaction mixture was cooled to room temperature, and then ethyl acetate and a saturated aqueous solution of sodium bicarbonate were added thereto. The organic layer was separated, washed with a saturated aqueous solution of sodium chloride, 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: 95-91% hexane/ethyl acetate] to obtain 0.17 g of tert-butyl 4-(3-(tert-butoxycarbonylamino)phenyl)-2-nitrobenzoate as a light yellow solid.

Workup

  1. temperatureby heating
  2. temperatureto reflux under a nitrogen atmosphere for 2 hours
  3. customThe organic layer was separated
  4. washwashed with a saturated aqueous solution of sodium chloride
  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: 95-91% hexane/ethyl acetate]

Sources & evidence

ORD record
ord-b7f6c180e2d945b98937b14d94f7d28c
Source dataset
uspto-grants-2013_07
Patent number
US08492582B2

Reaction notes

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