Ammonium Chloride → (7-bromo-1-methyl-1H-indol-2-yl)methanol

HRID 12625Notes

Reaction equation

HRID 12625 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[N:9]([CH3:11])[C:8]([C:12](OCC)=[O:13])=[CH:7]2.[BH4-].[Li+].[Cl-].[NH4+]>O1CCCC1>[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[N:9]([CH3:11])[C:8]([CH2:12][OH:13])=[CH:7]2

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 4148881Lithium borohydrideHCID 68693640ethyl 7-bromo-1-methyl-1H-indole-2-carboxylate

Product 1

HCID 68695245(7-bromo-1-methyl-1H-indol-2-yl)methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a tetrahydrofuran (40 mL) solution of ethyl 7-bromo-1-methyl-1H-indole-2-carboxylate (1.99 g), lithium tetrahydroborate (463 mg) was added at 0° C., followed by stirring at room temperature for 5 hours. To the reaction mixture, an aqueous saturated ammonium chloride solution was added, followed by extraction with ethyl acetate. The organic layer was washed in turn with water and saturated saline, dried over anhydrous sodium sulfate and then concentrated. The residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=90:10-70:30) to obtain the titled compound having the following physical properties (880 mg).

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe organic layer was washed in turn with water and saturated saline
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=90:10-70:30)

Sources & evidence

ORD record
ord-502f3206842346ae9fee5bc68ef8a314
Source dataset
uspto-grants-2010_06
Patent number
US07728023B2

Reaction notes

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