Sodium hydride → 8-Methoxy-3,4-dihydro-2H-pyrido[2',3':4,5]pyrrolo[2,1-b][1,3]oxazine

HRID 2298774Notes

Reaction equation

HRID 2298774 reaction equation
[H-].[Na+].Br[CH2:4][CH2:5][CH2:6][N:7]1[C:15]2[C:10](=[N:11][C:12]([O:16][CH3:17])=[CH:13][CH:14]=2)[CH2:9][C:8]1=[O:18]>CN(C)C=O>[CH3:17][O:16][C:12]1[CH:13]=[CH:14][C:15]2[N:7]3[C:8]([O:18][CH2:4][CH2:5][CH2:6]3)=[CH:9][C:10]=2[N:11]=1

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 112661091-(3-Bromopropyl)-5-methoxy-1,3-dihydro-2H-pyrrolo[3,2-b]pyridin-2-one

Product 1

HCID 114014538-Methoxy-3,4-dihydro-2H-pyrido[2',3':4,5]pyrrolo[2,1-b][1,3]oxazine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

Under an inert atmosphere, 160 mg (4 mmol) of sodium hydride (60% in oil) are added slowly at 0° C. to a solution of 380 mg (1.34 mmol) of the compound obtained in Step E in 10 ml of N,N-dimethylformamide. The reaction mixture is stirred at 0° C. for 30 minutes before being hydrolysed with ice and then extracted with ethyl acetate. The organic phase is washed several times with water, dried over magnesium sulphate, concentrated and purified by flash chromatography over silica gel (eluant: ethyl acetate/petroleum ether, 95:5) to yield the title compound in the form of a brown solid.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic phase is washed several times with water
  3. dry with materialdried over magnesium sulphate
  4. concentrationconcentrated
  5. custompurified by flash chromatography over silica gel (eluant: ethyl acetate/petroleum ether, 95:5)

Sources & evidence

ORD record
ord-d19eb1d7280245929710d3710968b380
Source dataset
uspto-grants-2002_12
Patent number
US06495543B1

Reaction notes

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