Sodium Cyanide → 4-(3-Isopropyl-1H-indol-5-yloxy)-3,5-bis-trifluoromethyl-phenylacetonitrile
Reaction equation
[C-:1]#[N:2].[Na+].[CH:4]([C:7]1[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([O:16][C:17]3[C:24]([C:25]([F:28])([F:27])[F:26])=[CH:23][C:20]([CH2:21]Br)=[CH:19][C:18]=3[C:29]([F:32])([F:31])[F:30])[CH:14]=2)[NH:9][CH:8]=1)([CH3:6])[CH3:5]>CN(C)C=O.O>[CH:4]([C:7]1[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([O:16][C:17]3[C:24]([C:25]([F:28])([F:27])[F:26])=[CH:23][C:20]([CH2:21][C:1]#[N:2])=[CH:19][C:18]=3[C:29]([F:32])([F:31])[F:30])[CH:14]=2)[NH:9][CH:8]=1)([CH3:6])[CH3:5]Participants
5
Conditions
- Temperature
- 50 °C
Procedure
72.9 mg (1.49 mmol) of sodium cyanide are added at 50° C. to a solution of 0.57 g (1.19 mmol) of benzyl bromide from Example VII in 3.5 ml of dimethylformamide and 0.38 ml of water and the mixture is stirred for 60 minutes at 50° C. Dimethylformamide is subsequently distilled off, the concentrate is diluted with ethyl acetate and water, and the aqueous phase is separated off and extracted again with ethyl acetate. The combined organic phases are washed with sodium chloride solution, dried over sodium sulphate, filtered and concentrated. The purification of the crude product is carried out on silica gel 60 by means of toluene/ethyl acetate (toluene, toluene/ethyl acetate=18:1 and 18:1.5).
Workup
- distillationDimethylformamide is subsequently distilled off
- additionthe concentrate is diluted with ethyl acetate and water
- customthe aqueous phase is separated off
- extractionextracted again with ethyl acetate
- washThe combined organic phases are washed with sodium chloride solution
- dry with materialdried over sodium sulphate
- filtrationfiltered
- concentrationconcentrated
- customThe purification of the crude product
Sources & evidence
- ORD record
- ord-45a44abab15f4950a55ade34bfbf4d21
- Source dataset
- uspto-grants-2004_09
- Patent number
- US06794406B2
Reaction notes
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