Sodium Carbonate → HCID 57942920, compound

HRID 1394186Notes

Reaction equation

HRID 1394186 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([N+:8]([O-:10])=[O:9])[CH:3]=1.C(=O)([O-])[O-].[Na+].[Na+].[C:17]([O:21][C:22]([N:24]1[CH:28]=[CH:27][CH:26]=[C:25]1B(O)O)=[O:23])([CH3:20])([CH3:19])[CH3:18]>COCCOC.C(O)C>[C:17]([O:21][C:22]([N:24]1[CH:28]=[CH:27][CH:26]=[C:25]1[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([N+:8]([O-:10])=[O:9])[CH:3]=1)=[O:23])([CH3:20])([CH3:18])[CH3:19]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 11457Benzene, 1-bromo-3-nitro-HCID 27343211-(tert-Butoxycarbonyl)-2-pyrroleboronic Acid

Product 1

HCID 57942920HCID 57942920, compoundYield 51%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

A solution of 1-bromo-3-nitrobenzene (1.5 g 7.42 mmol) in anhydrous 1,2-dimethoxyethane (10 ml) was treated sequentially with 1,1-bistriphenylphosphine palladium II dichloride (260 mg, 0.371 mmol), 2M aqueous sodium carbonate (7.4 ml), and 1-(t-Butoxycarbonyl)pyrrole-2-boronic acid (1.88 g, 8.91 mmol) dissolved in ethanol (10 ml). The reaction was heated under reflux for 5 hours under argon. The solvent was evaporated and the residue dissolved in dichloromethane, washed with water, brine, dried over anhydrous sodium sulfate, and evaporated in vacuo. The residue was purified by silica gel chromatography eluting with a mixture of ether/hexane (5:95) to afford the title compound (1.09 g, 51%); MS (ES+) m/e 288 [M+H]+.

Workup

  1. temperatureThe reaction was heated
  2. temperatureunder reflux for 5 hours under argon
  3. customThe solvent was evaporated
  4. dissolutionthe residue dissolved in dichloromethane
  5. washwashed with water, brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. customevaporated in vacuo
  8. customThe residue was purified by silica gel chromatography
  9. washeluting with a mixture of ether/hexane (5:95)

Sources & evidence

ORD record
ord-68de5c3bdd9540c992fb6fbf8bd58099
Source dataset
uspto-grants-2008_03
Patent number
US07348339B2

Reaction notes

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