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1-Bromo-2,4-difluorobenzene → (2S,4S)-1-Boc-4-[(2,4-difluorophenyl)amino]-2[(dimethylamino)carbonyl]pyrrolidine

HRID 1361335
Notes
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Reaction equation

HRID 1361335 reaction equation
[C:1]([N:8]1[CH2:12][C@@H:11]([NH2:13])[CH2:10][C@H:9]1[C:14]([N:16]([CH3:18])[CH3:17])=[O:15])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].CC(C)([O-])C.[Na+].C(P(C(C)(C)C)C1C=CC=CC=1C1C=CC=CC=1)(C)(C)C.Br[C:47]1[CH:52]=[CH:51][C:50]([F:53])=[CH:49][C:48]=1[F:54]>C1(C)C=CC=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.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[C:1]([N:8]1[CH2:12][C@@H:11]([NH:13][C:47]2[CH:52]=[CH:51][C:50]([F:53])=[CH:49][C:48]=2[F:54])[CH2:10][C@H:9]1[C:14]([N:16]([CH3:18])[CH3:17])=[O:15])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 676741-Bromo-2,4-difluorobenzeneHCID 27342152-(Di-tert-butylphosphino)biphenylHCID 23676156Sodium t-butoxideHCID 66971238tert-butyl (2S,4S)-4-amino-2-(dimethylcarbamoyl)pyrrolidine-1-carboxylate

Product 1

HCID 66970978(2S,4S)-1-Boc-4-[(2,4-difluorophenyl)amino]-2[(dimethylamino)carbonyl]pyrrolidineYield 78%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

To a solution of (2S,4S)-1-Boc-4-amino[(dimethylamino)carbonyl]pyrrolidine (8 g, 31.5 mmol) prepared in Step C in toluene (100 ml) was added sodium t-butoxide (3.46 g, 36 mmol), 2-(di-t-butylphosphino)biphenyl (800 mg, 2.68 mmol), tris(dibenzylideneacetone)dipalladium(0) (1.6 g, 1.79 mmol) and 1-bromo-2,4-difluorobenzene (6.94 g, 36 mmol), and the solution was stirred at 110° C. for 10 h. After the reaction finished, the solution was filtered through Celite, and extracted with water and EtOAc. The organic layer was dried over MgSO4, concentrated in vacuo, and purified by column chromatography (eluent, EtOAc/Hex=1/4) to give the title compound (1.5 g, 78%).

Workup

  1. filtrationthe solution was filtered through Celite
  2. extractionextracted with water and EtOAc
  3. dry with materialThe organic layer was dried over MgSO4
  4. concentrationconcentrated in vacuo
  5. custompurified by column chromatography (eluent, EtOAc/Hex=1/4)

Sources & evidence

ORD record
ord-8d6fcdda243c4b369bf8a8141f9acf90
Source dataset
uspto-grants-2011_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07879852B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes