1-[3-(Benzyloxy)propyl]-3,3-dibromo-5-methoxy-1,3-dihydro-2H-pyrrolo[3,2-b]pyridin-2-one → 1-[3-(Benzyloxy)propyl]-5-methoxy-1,3-dihydro-2h-pyrrolo[3,2-b]pyridin-2-one
Reaction equation
[CH2:1]([O:8][CH2:9][CH2:10][CH2:11][N:12]1[C:20]2[C:15](=[N:16][C:17]([O:21][CH3:22])=[CH:18][CH:19]=2)[C:14](Br)(Br)[C:13]1=[O:25])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(O)(=O)C.[Zn]>[CH2:1]([O:8][CH2:9][CH2:10][CH2:11][N:12]1[C:20]2[C:15](=[N:16][C:17]([O:21][CH3:22])=[CH:18][CH:19]=2)[CH2:14][C:13]1=[O:25])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1Participants
4
Procedure
Under argon and at room temperature, 1.10 g (16.8 mmol) of powdered zinc are added in portions to 789 mg (1.68 mmol) of the compound obtained in Step B dissolved in 15 ml of acetic acid. After 5 hours' stirring at room temperature, the reaction mixture is filtered using a Büchner funnel, evaporated to dryness and then coevaporated in the presence of toluene. The residue, which is taken up in ethyl acetate, is washed several times with water. The organic phase is dried over magnesium sulphate, filtered and concentrated and then purified by flash chromatography over silica gel (eluant:petroleum ether/ethyl acetate, 1:1) to yield the title compound in the form of an orange oil.
Workup
- filtrationthe reaction mixture is filtered
- customevaporated to dryness
- washis washed several times with water
- dry with materialThe organic phase is dried over magnesium sulphate
- filtrationfiltered
- concentrationconcentrated
- custompurified by flash chromatography over silica gel (eluant:petroleum ether/ethyl acetate, 1:1)
Sources & evidence
- ORD record
- ord-f8805e4e3c85466d8c22e40477d6389a
- Source dataset
- uspto-grants-2007_06
- Patent number
- US07235550B2
Reaction notes
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