Sodium Carbonate → 3-(2-Chloro-4-pyridin-3-yl-benzyl)-1-cyclohex-3-enyl-pyrrolidin-2-one

HRID 2235309Notes

Reaction equation

HRID 2235309 reaction equation
Br[C:2]1[CH:20]=[CH:19][C:5]([CH2:6][CH:7]2[CH2:11][CH2:10][N:9]([CH:12]3[CH2:17][CH2:16][CH:15]=[CH:14][CH2:13]3)[C:8]2=[O:18])=[C:4]([Cl:21])[CH:3]=1.[N:22]1[CH:27]=[CH:26][CH:25]=[C:24](B(O)O)[CH:23]=1.C([O-])([O-])=O.[Na+].[Na+].C([O-])(O)=O.[Na+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.COCCOC.O>[Cl:21][C:4]1[CH:3]=[C:2]([C:24]2[CH:23]=[N:22][CH:27]=[CH:26][CH:25]=2)[CH:20]=[CH:19][C:5]=1[CH2:6][CH:7]1[CH2:11][CH2:10][N:9]([CH:12]2[CH2:17][CH2:16][CH:15]=[CH:14][CH2:13]2)[C:8]1=[O:18]

Participants

8

Reactant 4

HCID 10340Sodium CarbonateHCID 516892Sodium BicarbonateHCID 27343783-Pyridinylboronic acidHCID 592994713-(4-Bromo-2-chloro-benzyl)-1-cyclohex-3-enyl-pyrrolidin-2-one

Product 1

HCID 592993513-(2-Chloro-4-pyridin-3-yl-benzyl)-1-cyclohex-3-enyl-pyrrolidin-2-oneYield 16.2%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

Combine 3-(4-bromo-2-chloro-benzyl)-1-cyclohex-3-enyl-pyrrolidin-2-one (370 mg, 1.01 mmol), 3-pyridine boronic acid (372 mg, 3.03 mmol), tetrakis(triphenylphosphine)palladium(0) (116 mg, 0.10 mmol), Na2CO3 (2.14 g, 20.2 mmols), water (1.5 mL), 1,2-dimethoxy-ethane (8 mL) and heat at 80° C. for 20 hours. Cool the reaction mixture to room temperature, add saturated aqueous NaHCO3 (5 mL) and extract with EtOAc (3×10 mL). Dry the organic layer over anhydrous Na2SO4, remove the solvent and purify the residue by chromatography over silica gel eluting with EtOAc in hexane (0 to 100%) to obtain 3-(2-chloro-4-pyridin-3-yl-benzyl)-1-cyclohex-3-enyl-pyrrolidin-2-one as a clear oil (60 mg, 16%): MS (ES+) m/z=367 (M+H)+.

Workup

  1. extractionextract with EtOAc (3×10 mL)
  2. dry with materialDry the organic layer over anhydrous Na2SO4
  3. customremove the solvent
  4. custompurify the residue by chromatography over silica gel eluting with EtOAc in hexane (0 to 100%)

Sources & evidence

ORD record
ord-ee824282c18a4d9795efdc5928b825ac
Source dataset
uspto-grants-2010_05
Patent number
US07713979B2

Reaction notes

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