N,N-Dimethylaniline → HCID 11998780, compound

HRID 2102735Notes

Reaction equation

HRID 2102735 reaction equation
C(=O)([O-])[O-].[Cs+].[Cs+].[CH3:7][N:8]([CH3:15])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.Br[C:17]1([CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[C:31]([Cl:35])[CH:30]=2)[C:25]2[C:20](=[CH:21][C:22]([Cl:26])=[CH:23][CH:24]=2)[NH:19][C:18]1=[O:27]>ClCCl>[Cl:26][C:22]1[CH:21]=[C:20]2[C:25]([C:17]([CH2:28][C:29]3[CH:34]=[CH:33][CH:32]=[C:31]([Cl:35])[CH:30]=3)([C:12]3[CH:13]=[CH:14][C:9]([N:8]([CH3:15])[CH3:7])=[CH:10][CH:11]=3)[C:18](=[O:27])[NH:19]2)=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 949N,N-DimethylanilineHCID 10796Cesium carbonateHCID 575072733-Bromo-6-chloro-3-(3-chloro-benzyl)-1,3-dihydro-indol-2-one

Product 1

HCID 11998780HCID 11998780, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To the suspension of cesium carbonate (0.147 g, 0.45 mmol) (Aldrich) in dichloromethane (2 mL) was added N,N-dimethylaniline (27.4 mg, 0.23 mmol) (Aldrich), followed by the addition of 3-bromo-6-chloro-3-(3-chloro-benzyl)-1,3-dihydro-indol-2-one (70 mg, 0.19 mmol) (from Example 60a supra) in dichloromethane (2 mL). The reaction mixture was stirred at room temperature for 24 hours. The reaction was quenched with water, extracted with dichloromethane three times. The combined organic layer was washed with water, brine, dried over MgSO4. After filtration, the solvent was removed. The residue was purified by chromatography to give rac-6-chloro-3-(3-chloro-benzyl)-3-(4-dimethylamino-phenyl)-1,3-dihydro-indol-2-one as a white solid. (Yield: 35 mg, 45%).

Workup

  1. customThe reaction was quenched with water
  2. extractionextracted with dichloromethane three times
  3. washThe combined organic layer was washed with water, brine
  4. dry with materialdried over MgSO4
  5. filtrationAfter filtration
  6. customthe solvent was removed
  7. customThe residue was purified by chromatography

Sources & evidence

ORD record
ord-4a2db9d08fe1491aba1c68a9da469a63
Source dataset
uspto-grants-2009_08
Patent number
US07576082B2

Reaction notes

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