Sodium Hydroxide → HCID 178434274, compound

HRID 2189166Notes

Reaction equation

HRID 2189166 reaction equation
[OH-].[Na+].[CH2:3]([O:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[C:14](=[O:16])[CH3:15])[CH:4]([CH3:6])[CH3:5].[CH3:17][C:18]1[C:26]2[C:21](=[CH:22][CH:23]=[C:24]([CH:27]=O)[CH:25]=2)[NH:20][N:19]=1>C(O)C>[CH2:3]([O:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[C:14](=[O:16])/[CH:15]=[CH:27]/[C:24]1[CH:25]=[C:26]2[C:21](=[CH:22][CH:23]=1)[NH:20][N:19]=[C:18]2[CH3:17])[CH:4]([CH3:6])[CH3:5]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 15741847HCID 15741847, compoundHCID 178434286HCID 178434286, compound

Product 1

HCID 178434274HCID 178434274, compoundYield 28.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of NaOH (0.2 g, 5 mmol) in 3 mL ethanol were added commercially available 1-(2-isobutoxyphenyl)ethanone (100 mg, 0.52 mmol) and commercially available 3-methyl-1H-indazole-5-carbaldehyde (200 mg, 1.25 mmol). The reaction mixture was stirred at room temperature for 24 h, concentrated under reduced pressure and the product was purified by SiO2 flash chromatography (60:40 hexanes/ethyl acetate) to afford (E)-1-(2-isobutoxyphenyl)-3-(3-methyl-1H-indazol-5-yl)prop-2-en-1-one (50 mg, 28.6%). C21H22N2O2: 335 (MH+).

Workup

  1. concentrationconcentrated under reduced pressure
  2. customthe product was purified by SiO2 flash chromatography (60:40 hexanes/ethyl acetate)

Sources & evidence

ORD record
ord-accaecacf64249e2ab4890e91db94bb7
Source dataset
uspto-grants-2012_12
Patent number
US08324231B2

Reaction notes

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