Dimethylformamide → HCID 58917751, compound

HRID 415700Notes

Reaction equation

HRID 415700 reaction equation
[CH:1]([C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]=[CH:6]2)=[O:2].[BrH+][CH2:13][C:14]1[CH:21]=[CH:20][C:17]([C:18]#[N:19])=[CH:16][CH:15]=1.[OH-].[K+].CN(C)C=O>O>[CH:1]([C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH2:13][C:14]1[CH:21]=[CH:20][C:17]([C:18]#[N:19])=[CH:16][CH:15]=1)[CH:7]=[CH:6]2)=[O:2]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 14797Potassium HydroxideHCID 589040Indole-5-carboxaldehydeHCID 178509646HCID 178509646, compound

Product 1

HCID 58917751HCID 58917751, compoundYield 84.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Mix 5-formylindole (0.50 g, 3.4 mmol), 4-bromniomethyl-benzonitrile (0.74 g, 3.8 mmol), powdered potassium hydroxide (0.23 g, 4.1 mmol) and dimethylformamide (7 mL) in a flask. Stir at rt overnight. Pour into water (20 mL) and extract with EtOAc/Hexanes (2:1, 3×50 mL). Evaporate solvents to give a yellow oil. Purification on silica using a 10% EtOAc/Hexanes to 30% EtOAc/Hexanes gradient eluent yields the product (0.75 g, 83%). Mass spectrum (ion spray): m/z=259.2 (M−1); 1H NMR (CDCl3) 10.04 (s, 1H), 8.20 (s, 1H), 7.75 (d, J=8.6 Hz, 1H), 7.60 (d, J=8.2 Hz, 2H), 7.28 (d, J=8.5 Hz, 1H), 7.22 (d, J=3.1 Hz, 1H), 7.15 (d, J=8.2 Hz, 2H), 6.77 (d, J=3.1 Hz, 1H), 5.44 (s, 2H).

Workup

  1. extractionextract with EtOAc/Hexanes (2:1, 3×50 mL)
  2. customEvaporate solvents to give a yellow oil
  3. customPurification on silica using a 10% EtOAc/Hexanes to 30% EtOAc/Hexanes gradient eluent

Sources & evidence

ORD record
ord-4c9a585f3241472c96364b60f23dcd91
Source dataset
uspto-grants-2012_01
Patent number
US08088800B2

Reaction notes

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