Potassium Iodide → 5-(1H-Indol-3-yl)pentanoic acid cyanomethyl ester
Reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH2:10][CH2:11][CH2:12][CH2:13][C:14]([OH:16])=[O:15])=[CH:2]1.C(=O)([O-])[O-].[Cs+].[Cs+].Cl[CH2:24][C:25]#[N:26].[I-].[K+]>CC(C)=O.CN(C)C=O>[C:25]([CH2:24][O:15][C:14](=[O:16])[CH2:13][CH2:12][CH2:11][CH2:10][C:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[NH:1][CH:2]=1)#[N:26]Participants
7
Procedure
5-(1H-Indol-3-yl)pentanoic acid (5 g, 23 mmol) was dissolved in a mixture of acetone (25 ml) and dimethylformamide (25 ml), and caesium carbonate (3.75 g, 11.5 mmol), chloroacetonitrile (2.16 ml, 34.5 mmol) and potassium iodide (20 mg) were added in succession. After 6.5 h at 60° C. and 16 h at RT, the solid residues were filtered off and washed with acetone (2×30 ml) and the filtrate was concentrated. The crude product was purified by chromatography on silica gel (130 g) with EA/cyclohexane (1:3). The product was obtained as a colourless solid with an m.p. of 76° C. in a yield of 77% (4.53 g).
Workup
- additionwere added in succession
- filtration16 h at RT, the solid residues were filtered off
- washwashed with acetone (2×30 ml)
- concentrationthe filtrate was concentrated
- customThe crude product was purified by chromatography on silica gel (130 g) with EA/cyclohexane (1:3)
- customThe product was obtained as a colourless solid with an m.p. of 76° C. in a yield of 77% (4.53 g)
Sources & evidence
- ORD record
- ord-a61b9df88b1f4fec8b934976358ea9f2
- Source dataset
- uspto-grants-2011_09
- Patent number
- US08017630B2
Reaction notes
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