Toluene → 4-(3-Isopropyl-1H-indol-5-yloxy)-3,5-dichlorophenylacetonitrile

HRID 1007489Notes

Reaction equation

HRID 1007489 reaction equation
[CH:1]([C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([O:13][C:14]3[C:21]([Cl:22])=[CH:20][C:17]([CH2:18]Br)=[CH:16][C:15]=3[Cl:23])[CH:11]=2)[NH:6][CH:5]=1)([CH3:3])[CH3:2].[C-:24]#[N:25].[Na+].C1(C)C=CC=CC=1>CN(C=O)C.O>[CH:1]([C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([O:13][C:14]3[C:21]([Cl:22])=[CH:20][C:17]([CH2:18][C:24]#[N:25])=[CH:16][C:15]=3[Cl:23])[CH:11]=2)[NH:6][CH:5]=1)([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 1140TolueneHCID 8929Sodium CyanideHCID 226696244-(3-Isopropyl-1H-indol-5-yloxy)-3,5-dichlorobenzyl bromide

Product 1

HCID 226698504-(3-Isopropyl-1H-indol-5-yloxy)-3,5-dichlorophenylacetonitrile

Reagents, catalysts & solvents 1

HCID 21962138N,N-Dimethylformamide--water (1/1)Solvent

Procedure

Analogously to the procedure of Example VIII, 1.0 g (2.42 mmol) of benzyl bromide from Example XVIII is reacted with 0.15 g (3.03 mmol) of sodium cyanide in DMF/H2O (10:1) at 50° C. in 60 min. After isolation of the crude product (distilling off DMF and quenching with ethyl acetate/water), chromatography is carried out on silica gel 60 by means of toluene.

Sources & evidence

ORD record
ord-a93689e779454e00ad3b8288f53b9425
Source dataset
uspto-grants-2004_09
Patent number
US06794406B2

Reaction notes

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