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Cesium carbonate → 1-(5-Tert-butyl-2-methoxy-3-nitro-phenyl)-pyrrolidin-2-one

HRID 1181935
Notes
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Reaction equation

HRID 1181935 reaction equation
Br[C:2]1[CH:7]=[C:6]([C:8]([CH3:11])([CH3:10])[CH3:9])[CH:5]=[C:4]([N+:12]([O-:14])=[O:13])[C:3]=1[O:15][CH3:16].[NH:17]1[CH2:21][CH2:20][CH2:19][C:18]1=[O:22].C1(P(C2C=CC=CC=2)C2C3OC4C(=CC=CC=4P(C4C=CC=CC=4)C4C=CC=CC=4)C(C)(C)C=3C=CC=2)C=CC=CC=1.C([O-])([O-])=O.[Cs+].[Cs+]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[C:8]([C:6]1[CH:5]=[C:4]([N+:12]([O-:14])=[O:13])[C:3]([O:15][CH3:16])=[C:2]([N:17]2[CH2:21][CH2:20][CH2:19][C:18]2=[O:22])[CH:7]=1)([CH3:11])([CH3:10])[CH3:9]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 10796Cesium carbonateHCID 120252-PyrrolidoneHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 575500241-Bromo-5-(tert-butyl)-2-methoxy-3-nitrobenzene

Product 1

HCID 575500321-(5-Tert-butyl-2-methoxy-3-nitro-phenyl)-pyrrolidin-2-oneYield 30%

Reagents, catalysts & solvents

1
HCID 9811564Bis(dibenzylideneacetone)palladiumCatalyst

Procedure

An oven-dried Schienk tube was charged with 2-bromo-4-tert-butyl-6-nitroanisole (500 mg, 1.74 mmol), 2-pyrrolidinone (158 μL, 2.09 mmol), Pd2(dba)3 (32 mg, 0.035 mmol), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (58 mg, 0.1 mmol) and Cs2CO3 (795 mg, 2.44 mmol). The tube was capped with a rubber septum, purged with argon and 1,4-dioxane (7 mL) was then added through the septum via a syringe. The tube was sealed with a teflon screwcap, and the reaction mixture was stirred at 100 C for 20 h. The reaction mixture was cooled to room temperature, diluted with EtOAc (100 mL), washed with water, brine and dried over anhydrous Na2SO4. The solvent was removed in vacuo, and crude product was purified by column chromatography (2:1 hexane-EtOAc) to give 1-(5-tert-butyl-2-methoxy-3-nitro-phenyl)-pyrrolidin-2-one (150 mg, 30%).

Workup

  1. customThe tube was capped with a rubber septum
  2. custompurged with argon and 1,4-dioxane (7 mL)
  3. additionwas then added through the septum via a syringe
  4. customThe tube was sealed with a teflon screwcap
  5. additiondiluted with EtOAc (100 mL)
  6. washwashed with water, brine
  7. dry with materialdried over anhydrous Na2SO4
  8. customThe solvent was removed in vacuo, and crude product
  9. customwas purified by column chromatography (2:1 hexane-EtOAc)

Sources & evidence

ORD record
ord-50191ba87d004e59a5ca6a188ad951fe
Source dataset
uspto-grants-2007_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07285545B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes