2-Chloroethyl isocyanate → 1-(2-chloroethyl)-3-[4-(3-cyano-1-ethyl-6-methoxy-1H-indol-2-yl)-phenyl]-urea

HRID 1009620Notes

Reaction equation

HRID 1009620 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

Reactant 2

HCID 160352-Chloroethyl isocyanateHCID 116017362-(4-aminophenyl)-1-ethyl-6-methoxy-1H-indole-3-carbonitrile

Product 1

HCID 594254191-(2-chloroethyl)-3-[4-(3-cyano-1-ethyl-6-methoxy-1H-indol-2-yl)-phenyl]-ureaYield 91%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-(4-aminophenyl)-1-ethyl-6-methoxy-1H-indole-3-carbonitrile (50 mg, 0.172 mmol) in THF (2 mL) is added 2-chloroethyl isocyanate (22 uL, 0.258 mmol) at room temperature. After stirring overnight at reflux, the reaction mixture is concentrated in vacuo and the residue is diluted with ethyl acetate. The resulting semi-solid is triturated with hexane and the precipitate collected is 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

  1. temperatureat reflux
  2. concentrationthe reaction mixture is concentrated in vacuo
  3. additionthe residue is diluted with ethyl acetate
  4. customThe resulting semi-solid is triturated with hexane
  5. customthe precipitate collected
  6. filtrationis collected by filtration
  7. washwashed well with 50% ethyl acetate in hexane
  8. customdried in vacuo

Sources & evidence

ORD record
ord-06c7bdda03e64c998edb13dbc76af6c3
Source dataset
uspto-grants-2011_07
Patent number
US07973069B2

Reaction notes

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