Sodium hydride → HCID 178526264, compound

HRID 748531Notes

Reaction equation

HRID 748531 reaction equation
[H-].[Na+].[N:3]1[CH:8]=[CH:7][CH:6]=[C:5]([C:9]2[CH:10]=[C:11]3[C:15](=[CH:16][CH:17]=2)[NH:14][C:13](=[O:18])[CH2:12]3)[CH:4]=1.Cl[C:20]1[CH:25]=[CH:24][C:23]([CH2:26][N:27]2[CH2:32][CH2:31][O:30][CH2:29][CH2:28]2)=[CH:22][N+:21]=1[O-:33]>CN(C)C=O>[N:27]1([CH2:26][C:23]2[CH:24]=[CH:25][C:20]([C:12]3[C:11]4[C:15](=[CH:16][CH:17]=[C:9]([C:5]5[CH:4]=[N:3][CH:8]=[CH:7][CH:6]=5)[CH:10]=4)[NH:14][C:13]=3[OH:18])=[N+:21]([O-:33])[CH:22]=2)[CH2:32][CH2:31][O:30][CH2:29][CH2:28]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 12050204HCID 12050204, compoundHCID 85873132HCID 85873132, compound

Product 1

HCID 178526264HCID 178526264, compoundYield 82.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Conditions

Temperature
130 °C

Procedure

To a suspension of sodium hydride (0.05 g, 1.2 mmol, 60% dispersion in oil, pre-washed with hexane) in N,N-dimethylformamide (3 mL) was added a solution of 5-pyridin-3-yl-1,3-dihydro-2H-indol-2-one (0.19 g, 0.90 mmol) in N,N-dimethylformamide (4 mL). The mixture was stirred for 20 min under nitrogen atmosphere. 2-Chloro-5-(morpholin-4-ylmethyl)pyridine 1-oxide (0.14 g, 0.60 mmol), dissolved in N,N-dimethylformamide (3 mL) was added dropwise and the mixture was stirred at room temperature for 2 h and then heated at 130° C. for 1.5 h. The solvent was evaporated in vacuo and the residue was partitioned between 2 M HCl and ethyl acetate and the phases were separated. The aqueous layer was alkalized by addition of NaHCO3 (s) and extracted with ethyl acetate. The organic layer was dried (Na2SO4) and the solvent was removed in vacuo affording 200 mg of the title compound as a yellow solid: MS (ES) m/z 403 (M++1).

Workup

  1. additionwas added dropwise
  2. stirringthe mixture was stirred at room temperature for 2 h
  3. customThe solvent was evaporated in vacuo
  4. customthe residue was partitioned between 2 M HCl and ethyl acetate
  5. customthe phases were separated
  6. additionThe aqueous layer was alkalized by addition of NaHCO3 (s)
  7. extractionextracted with ethyl acetate
  8. dry with materialThe organic layer was dried (Na2SO4)
  9. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-bf24637a24874f8993ce87b74853f523
Source dataset
uspto-grants-2008_07
Patent number
US07399780B2

Reaction notes

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