Hydroxide → 2-Methyl-4-morpholino-5-fluoroindole

HRID 434678Notes

Reaction equation

HRID 434678 reaction equation
[CH3:1][C:2]1[NH:3][C:4]2[C:9]([CH:10]=1)=[C:8]([N:11]1[CH2:16][CH2:15][O:14][CH2:13][CH2:12]1)[C:7]([F:17])=[CH:6][C:5]=2Br.[OH-].[H][H]>C(O)C.[C].[Pd]>[CH3:1][C:2]1[NH:3][C:4]2[C:9]([CH:10]=1)=[C:8]([N:11]1[CH2:12][CH2:13][O:14][CH2:15][CH2:16]1)[C:7]([F:17])=[CH:6][CH:5]=2

Participants

6

Reactant 3

HCID 961HydroxideHCID 202589932-Methyl-4-morpholino-5-fluoro-7-bromoindoleHCID 178418361HCID 178418361, compound

Product 1

HCID 202589922-Methyl-4-morpholino-5-fluoroindoleYield 65.7%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

To a solution of 24 g of 2-methyl-4-morpholino-5-fluoro-7-bromoindole in 200 ml of ethanol was added 1 g of palladium-carbon and then 15 ml of a 20% aqueous sodiium hydroxide solution. This mixture was subjected to catalytic reduction at room temperature and at atmospheric pressure. The reaction was stopped when a theoretical amount (about 1.7 l) of hydrogen was absorbed, and the catalyst was removed by filtration followed by concentration. The residue was purified through silica gel column chromatography (Wako gel C-200; eluent:chloroform:n-hexane=5:1) to give 11.8 g of 2-methyl-4-morpholino-5-fluoroindole.

Workup

  1. customwas subjected to catalytic reduction at room temperature and at atmospheric pressure
  2. customwas absorbed
  3. customthe catalyst was removed by filtration
  4. concentrationfollowed by concentration
  5. customThe residue was purified through silica gel column chromatography (Wako gel C-200; eluent:chloroform:n-hexane=5:1)

Sources & evidence

ORD record
ord-f82e5e9786934fb2a560732e42ba15b4
Source dataset
uspto-grants-1983_08
Patent number
US04399134

Reaction notes

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