2-Chloroethyl isocyanate → HCID 59425711, compound

HRID 252530Notes

Reaction equation

HRID 252530 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]#[C:9][C:10]2[N:11]([CH2:23][CH3:24])[C:12]3[C:17]([C:18]=2[C:19]#[N:20])=[CH:16][CH:15]=[C:14]([O:21][CH3:22])[CH:13]=3)=[CH:4][CH:3]=1.[Cl:25][CH2:26][CH2:27][N:28]=[C:29]=[O:30]>C1(C)C=CC=CC=1.CC(C)=O>[Cl:25][CH2:26][CH2:27][NH:28][C:29]([NH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]#[C:9][C:10]2[N:11]([CH2:23][CH3:24])[C:12]3[C:17]([C:18]=2[C:19]#[N:20])=[CH:16][CH:15]=[C:14]([O:21][CH3:22])[CH:13]=3)=[CH:4][CH:3]=1)=[O:30]

Participants

5

Reactant 2

HCID 160352-Chloroethyl isocyanateHCID 11587731HCID 11587731, compound

Product 1

HCID 59425711HCID 59425711, compoundYield 54.2%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

2-(4-Aminophenylethynyl)-1-ethyl-6-methoxy-1H-indole-3-carbonitrile (100 mg, 0.32 mmol), prepared as described in Example 1H, is suspended in toluene (600 μL). 2-Chloroethyl isocyanate (32 μL, 0.37 mmol) is added, and the mixture is heated at 100° C. for 5 h. The reaction mixture is then cooled, diluted in acetone, and absorbed onto silica. Purification by column chromatography (5-10% EtOAc in CH2Cl2) yields 1-(2-chloro-ethyl)-3-[4-(3-cyano-1-ethyl-6-methoxy-1H-indol-2-ylethynyl)-phenyl]urea (73 mg, 54%) as a yellow solid.

Workup

  1. temperatureThe reaction mixture is then cooled
  2. customabsorbed onto silica
  3. customPurification by column chromatography (5-10% EtOAc in CH2Cl2)

Sources & evidence

ORD record
ord-6b636e1b2a0b41f582defd803c929648
Source dataset
uspto-grants-2011_01
Patent number
US07868037B2

Reaction notes

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