1,2-Dimethoxyethane → t-Butyl 2-(5-ethoxycarbonyl-2-methoxymethoxy-phenyl)-pyrrole-1-carboxylate

HRID 13260Notes

Reaction equation

HRID 13260 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH:12]=[CH:11][CH:10]=[C:9]1B(O)O)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[Na+].[Na+].C(COC)OC.Br[C:29]1[CH:30]=[C:31]([CH:37]=[CH:38][C:39]=1[O:40][CH2:41][O:42][CH3:43])[C:32]([O:34][CH2:35][CH3:36])=[O:33]>O>[CH2:35]([O:34][C:32]([C:31]1[CH:30]=[CH:29][C:39]([O:40][CH2:41][O:42][CH3:43])=[C:38]([C:9]2[N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH:12]=[CH:11][CH:10]=2)[CH:37]=1)=[O:33])[CH3:36]

Participants

6

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 10340Sodium CarbonateHCID 27343211-(tert-Butoxycarbonyl)-2-pyrroleboronic AcidHCID 23145548Ethyl 3-bromo-4-methoxymethoxybenzoate

Product 1

HCID 23145511t-Butyl 2-(5-ethoxycarbonyl-2-methoxymethoxy-phenyl)-pyrrole-1-carboxylate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

21 g of 1-(t-butoxycarbonyl)pyrrole-2-boronic acid, 4.2 g of tetrakistriphenylphosphine palladium and 153 ml of aqueous sodium carbonate solution (2 M) were added in order to a dimethoxyethane (350 ml) solution of 21 g of ethyl 3-bromo-4-methoxymethoxybenzoate, and the reaction liquid was heated overnight under reflux in a nitrogen atmosphere. After cooled, the reaction liquid was diluted with water, extracted with chloroform, and dried with anhydrous magnesium sulfate. The solvent was evaporated away under reduced pressure, and the resulting residue was purified through silica gel column chromatography (developing solvent: hexane/ethyl acetate=12/1 to 10/1) to obtain the entitled compound as a white solid.

Workup

  1. customthe reaction liquid
  2. temperaturewas heated overnight
  3. temperatureunder reflux in a nitrogen atmosphere
  4. temperatureAfter cooled
  5. customthe reaction liquid
  6. extractionextracted with chloroform
  7. dry with materialdried with anhydrous magnesium sulfate
  8. customThe solvent was evaporated away under reduced pressure
  9. customthe resulting residue was purified through silica gel column chromatography (developing solvent: hexane/ethyl acetate=12/1 to 10/1)

Sources & evidence

ORD record
ord-d30478f937364bbaa89c361b79ded6f3
Source dataset
uspto-grants-2010_06
Patent number
US07728025B2

Reaction notes

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