Trimethylamine → (2E)-1-(7-bromo-1-methylindol-2-yl)-2-hydrazinylideneethanone

HRID 12622

Reaction equation

HRID 12622 reaction equation
C[Si]([CH:5]=[N+:6]=[N-:7])(C)C.CN(C)C.[Br:12][C:13]1[CH:14]=[CH:15][CH:16]=[C:17]2[C:21]=1[N:20]([CH3:22])[C:19]([C:23](Cl)=[O:24])=[CH:18]2.[Cl-].[NH4+]>O1CCCC1.C(#N)C>[Br:12][C:13]1[CH:14]=[CH:15][CH:16]=[C:17]2[C:21]=1[N:20]([CH3:22])[C:19]([C:23](=[O:24])/[CH:5]=[N:6]/[NH2:7])=[CH:18]2

Participants

7

Reactant 4

HCID 1146TrimethylamineHCID 25517Ammonium ChlorideHCID 167693TrimethylsilyldiazomethaneHCID 875414197-bromo-1-methyl-1H-indole-2-carboxylic acid chloride

Product 1

HCID 145729974(2E)-1-(7-bromo-1-methylindol-2-yl)-2-hydrazinylideneethanone

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a dichloromethane (2 mL) solution of 7-bromo-1-methyl-1H-indole-2-carboxylic acid (200 mg), oxalyl dichloride (0.10 mL) and N,N-dimethylformamide (5 mL) were added and the mixture was stirred at room temperature for 2 hours. The reaction mixture was concentrated, azeotroped twice with toluene to obtain a crude product of 7-bromo-1-methyl-1H-indole-2-carboxylic acid chloride. Separately, a solution was prepared by dissolving 2M trimethylsilyldiazomethane (0.60 mL) and trimethylamine (0.16 mL) in tetrahydrofuran (2 mL)-acetonitrile (2 mL) and a tetrahydrofuran (1 mL)acetonitrile (1 mL) solution of 7-bromo-1-methyl-1H-indole-2-carboxylic acid chloride was added thereto, and then the mixture was stirred at room temperature for 4 hours. To the reaction mixture, an aqueous saturated ammonium chloride solution was added, followed by extraction with ethyl acetate. The organic layer was washed with 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 85:15) to obtain the titled compound having the following physical properties (72 mg).

Workup

  1. customSeparately, a solution was prepared
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe organic layer was washed with saturated saline
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=90:10 85:15)

Sources & evidence

ORD record
ord-757e66c04e504a789c6f1879b02fcaff
Source dataset
uspto-grants-2010_06
Patent number
US07728023B2

Linked notes

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