5-({5-[2-(benzyloxy)ethyl]-3-ethyl-1H-pyrazol-4-yl}oxy)isophthalonitrile → 5-{[3-Ethyl-5-(2-hydroxyethyl)-1H-pyrazol-4-yl]oxy}isophthalonitrile
Reaction equation
C([O:8][CH2:9][CH2:10][C:11]1[NH:15][N:14]=[C:13]([CH2:16][CH3:17])[C:12]=1[O:18][C:19]1[CH:20]=[C:21]([C:27]#[N:28])[CH:22]=[C:23]([CH:26]=1)[C:24]#[N:25])C1C=CC=CC=1>ClCCl.[Fe](Cl)(Cl)Cl>[CH2:16]([C:13]1[C:12]([O:18][C:19]2[CH:26]=[C:23]([C:24]#[N:25])[CH:22]=[C:21]([CH:20]=2)[C:27]#[N:28])=[C:11]([CH2:10][CH2:9][OH:8])[NH:15][N:14]=1)[CH3:17]Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
Iron(III)Chloride (217 mg, 1.30 mmol) was added to a solution of the pyrazole from Example 153 (50 mg, 0.13 mmol) in dichloromethane (5 ml) under nitrogen at room temperature. After stirring for 30 minutes the mixture was diluted with dichloromethane (20 ml), washed with water (100 ml) then saturated aqueous sodium ethylenediaminetetraacetate solution (20 ml), dried over magnesium sulphate and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel eluting with dichloromethane:methanol (98:2 changing to 95:5, by volume) to provide the title compound (20 mg) as a white solid.
Workup
- washwashed with water (100 ml)
- dry with materialsaturated aqueous sodium ethylenediaminetetraacetate solution (20 ml), dried over magnesium sulphate
- concentrationconcentrated under reduced pressure
- customThe residue was purified by flash chromatography on silica gel eluting with dichloromethane:methanol (98:2 changing to 95:5, by volume)
Sources & evidence
- ORD record
- ord-4db62a59310b4f65ba2e5b1ba6d25e1d
- Source dataset
- uspto-grants-2006_09
- Patent number
- US07109228B2
Reaction notes
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