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alpha-Bromo-o-chlorotoluene → (S)-2-chloro-4-((2-chlorobenzyl)(1-methyl-5-oxopyrrolidin-3-yl)amino)benzonitrile

HRID 1160414
Notes
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Reaction equation

HRID 1160414 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:11]=[C:10]([NH:12][C@H:13]2[CH2:17][C:16](=[O:18])[N:15]([CH3:19])[CH2:14]2)[CH:9]=[CH:8][C:5]=1[C:6]#[N:7].Br[CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[Cl:28]>CN(C=O)C>[Cl:3][C:4]1[CH:11]=[C:10]([N:12]([CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[Cl:28])[C@H:13]2[CH2:17][C:16](=[O:18])[N:15]([CH3:19])[CH2:14]2)[CH:9]=[CH:8][C:5]=1[C:6]#[N:7]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 11905alpha-Bromo-o-chlorotolueneHCID 24758Sodium hydrideHCID 595161672-Chloro-4-{[(3S)-1-methyl-5-oxo-3-pyrrolidinyl]amino}benzonitrile

Product 1

HCID 45271113(S)-2-chloro-4-((2-chlorobenzyl)(1-methyl-5-oxopyrrolidin-3-yl)amino)benzonitrileYield 37%

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent

Procedure

NaH (60% in mineral oil, 0.010 g, 0.26 mmol) was added to a solution of 2-chloro-4-{[(3S)-1-methyl-5-oxo-3-pyrrolidinyl]amino}benzonitrile (0.06 g, 0.24 mmol) in DMF (2 mL) at 0° C. under a N2 atmosphere. After stirring for 10 min, 1-(bromomethyl)-2-chlorobenzene (0.054 g, 0.26 mmol) was added and the reaction mixture was stirred at 0° C. for 15 min. The reaction was quenched with H2O and then partitioned between EtOAc and H2O. The organic layer was dried over Na2SO4, filtered, and concentrated. The residue was purified via column chromatography with 5% EtOAc in hexane grading to 100% EtOAc in hexane to yield the titled compound (0.03 g, 37%) as a clear oil. 1H-NMR (CDCl3) δ: 2.486 (1H, m), 2.797 (1H, m), 2.866 (3H, s), 3.383 (1H, m), 3.785 (1H, m), 4.563 (2H, m), 4.281 (1H, m), 6.519 (1H, dd, J=8.8 Hz, 2.8 Hz), 6.717 (1H, d, J=2.8 Hz), 6.757 (1H, dd, J=7.6 Hz, 1.2 Hz), 7.264 (2H, m), 7.420 (2H, m). LC-MS (ES) m/e 374.2 (M+H)+.

Workup

  1. stirringthe reaction mixture was stirred at 0° C. for 15 min
  2. customThe reaction was quenched with H2O
  3. custompartitioned between EtOAc and H2O
  4. dry with materialThe organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified via column chromatography with 5% EtOAc in hexane grading to 100% EtOAc in hexane

Sources & evidence

ORD record
ord-f83fd6a55c5b4ecf87838a30a3fe3dbb
Source dataset
uspto-grants-2010_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07816395B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes