Sodium Carbonate → Tert-butyl 4-(isoquinolin-4-yl)-2-nitrobenzoate

HRID 454512Notes

Reaction equation

HRID 454512 reaction equation
C(=O)([O-])[O-].[Na+].[Na+].CC1(C)C(C)(C)OB([C:15]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[CH:18]=[N:17][CH:16]=2)O1.Br[C:27]1[CH:39]=[CH:38][C:30]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])=[C:29]([N+:40]([O-:42])=[O:41])[CH:28]=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.O.C(OCC)(=O)C.COCCOC>[CH:18]1[C:19]2[C:24](=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:15]([C:27]2[CH:39]=[CH:38][C:30]([C:31]([O:33][C:34]([CH3:36])([CH3:37])[CH3:35])=[O:32])=[C:29]([N+:40]([O-:42])=[O:41])[CH:28]=2)=[CH:16][N:17]=1

Participants

8

Reactant 3

HCID 10340Sodium CarbonateHCID 27605944-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)isoquinolineHCID 26369829tert-Butyl 4-bromo-2-nitrobenzoate

Product 1

HCID 58508799Tert-butyl 4-(isoquinolin-4-yl)-2-nitrobenzoateYield 100%

Reagents, catalysts & solvents 4

HCID 178418476HCID 178418476, compoundCatalystHCID 962WaterSolvent2×HCID 80711,2-DimethoxyethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Water (15 mL), sodium carbonate (4.6 g), 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)isoquinoline (5.1 g), and bis(triphenylphosphine)palladium(II) dichloride (0.24 g) were added to an ethylene glycol dimethyl ether (50 mL) solution of tert-butyl 4-bromo-2-nitrobenzoate (5.0 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 water 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: 85-75% hexane/ethyl acetate] to obtain 5.8 g of tert-butyl 4-(isoquinolin-4-yl)-2-nitrobenzoate as a brown oily substance.

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: 85-75% hexane/ethyl acetate]

Sources & evidence

ORD record
ord-c5f00effe90b46de926f3c225148c73c
Source dataset
uspto-grants-2013_07
Patent number
US08492582B2

Reaction notes

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