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Water → t-Butyl 2-(4-amino-2-(4-methanesulfonyl-phenoxy)-5-nitro-phenyl)-pyrrole-1-carboxylate

HRID 13342
Notes
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Reaction equation

HRID 13342 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+].O.Br[C:24]1[C:29]([O:30][C:31]2[CH:36]=[CH:35][C:34]([S:37]([CH3:40])(=[O:39])=[O:38])=[CH:33][CH:32]=2)=[CH:28][C:27]([NH2:41])=[C:26]([N+:42]([O-:44])=[O:43])[CH:25]=1>C(COC)OC>[NH2:41][C:27]1[C:26]([N+:42]([O-:44])=[O:43])=[CH:25][C:24]([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)=[C:29]([O:30][C:31]2[CH:32]=[CH:33][C:34]([S:37]([CH3:40])(=[O:39])=[O:38])=[CH:35][CH:36]=2)[CH:28]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 27343211-(tert-Butoxycarbonyl)-2-pyrroleboronic AcidHCID 231452284-Bromo-5-(4-methanesulfonyl-phenoxy)-2-nitro-phenylamine

Product 1

HCID 23145143t-Butyl 2-(4-amino-2-(4-methanesulfonyl-phenoxy)-5-nitro-phenyl)-pyrrole-1-carboxylate

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
80 °C

Procedure

7.9 g of 1-(t-butoxycarbonyl)pyrrole-2-boronic acid, 1.8 g of dichlorobistriphenylphosphine palladium, 50 ml of aqueous saturated sodium carbonate solution and 50 ml of water were added in order to a dimethoxyethane (100 ml) solution of 10.3 g of 4-bromo-5-(4-methanesulfonyl-phenoxy)-2-nitro-phenylamine, and the reaction liquid was stirred in a nitrogen atmosphere at 80° C. for 1 hour. After cooled, the reaction liquid was filtered through Celite, the filtrate was diluted with ethyl acetate, washed with water and saturated saline in order, and then 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=1/1) to obtain the entitled compound as a brown oily substance.

Workup

  1. customthe reaction liquid
  2. temperatureAfter cooled
  3. customthe reaction liquid
  4. filtrationwas filtered through Celite
  5. additionthe filtrate was diluted with ethyl acetate
  6. washwashed with water and saturated saline in order
  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=1/1)
  10. customto obtain the entitled compound as a brown oily substance

Sources & evidence

ORD record
ord-84d1dd9f7dda4836b1bb8da6482e292d
Source dataset
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07728025B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes