Indole-3-acetonitrile → HCID 22607581, compound

HRID 2307783Notes

Reaction equation

HRID 2307783 reaction equation
[C:1]([CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6][CH:5]=1)#[N:2].[O-]CC.[Na+].[Br:17][C:18]1[CH:19]=[N:20][CH:21]=[C:22]([CH:24]=O)[CH:23]=1>C(O)C>[Br:17][C:18]1[CH:23]=[C:22](/[CH:24]=[C:3](/[C:4]2[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[NH:6][CH:5]=2)\[C:1]#[N:2])[CH:21]=[N:20][CH:19]=1

Participants

5

Reactant 3

HCID 351795Indole-3-acetonitrileHCID 2723922Sodium ethoxideHCID 27847345-Bromo-3-pyridinecarboxaldehyde

Product 1

HCID 22607581HCID 22607581, compoundYield 16%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A solution of 3-cyanomethylindole (156 mg, 1.0 mmol) in anhydrous ethanol (1.5 mL) at room temperature was treated with 21% sodium ethoxide in ethanol (450 μL), stirred for 1 hour, treated with 3-bromopyridine-5-carboxaldehyde (J. Heterocycl. Chem., 1995, 32, 1801.) (187 mg, 1.0 mmol), stirred overnight, and concentrated. The residue was purified by flash column chromatography on silica gel with 2% methanol/dichloromethane to provide the desired product (52 mg, 16%). MS (DCI/NH3) m/e 325 (M+H)+.

Workup

  1. stirringstirred overnight
  2. concentrationconcentrated
  3. customThe residue was purified by flash column chromatography on silica gel with 2% methanol/dichloromethane

Sources & evidence

ORD record
ord-c0143c4c12084dfe9a45cc8a7b514e4b
Source dataset
uspto-grants-2004_12
Patent number
US06831175B2

Reaction notes

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