2-Chloroethyl isocyanate → 1-(2-chloroethyl)-3-[4-(3-cyano-1-ethyl-6-methoxy-1H-indol-2-yl)-phenyl]-urea
Reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]([CH2:21][CH3:22])[C:10]3[C:15]([C:16]=2[C:17]#[N:18])=[CH:14][CH:13]=[C:12]([O:19][CH3:20])[CH:11]=3)=[CH:4][CH:3]=1.[Cl:23][CH2:24][CH2:25][N:26]=[C:27]=[O:28]>C1COCC1>[Cl:23][CH2:24][CH2:25][NH:26][C:27]([NH:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:9]([CH2:21][CH3:22])[C:10]3[C:15]([C:16]=2[C:17]#[N:18])=[CH:14][CH:13]=[C:12]([O:19][CH3:20])[CH:11]=3)=[CH:6][CH:7]=1)=[O:28]Participants
4
Procedure
To solution of 2-(4-aminophenyl)-1-ethyl-6-methoxy-1H-indole-3-carbonitrile (50 mg, 0.172 mmole) in THF (2 mL) was added 2-chloroethyl isocyanate (22 uL, 0.258 mmole) at room temperature. After stirring overnight at reflux, the reaction mixture was concentrated in vacuo and the residue was diluted with ethyl acetate. The resulting semi-solid was triturated with hexane and the precipitate collected was collected by filtration and washed well with 50% ethyl acetate in hexane and dried in vacuo to afford (62 mg, 91%) of 1-(2-chloroethyl)-3-[4-(3-cyano-1-ethyl-6-methoxy-1H-indol-2-yl)-phenyl]-urea.
Workup
- temperatureat reflux
- concentrationthe reaction mixture was concentrated in vacuo
- additionthe residue was diluted with ethyl acetate
- customThe resulting semi-solid was triturated with hexane
- customthe precipitate collected
- filtrationwas collected by filtration
- washwashed well with 50% ethyl acetate in hexane
- customdried in vacuo
Sources & evidence
- ORD record
- ord-78928e5f69604e049c8625d984a72c8e
- Source dataset
- uspto-grants-2011_09
- Patent number
- US08013006B2
Reaction notes
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