Ethyl isocyanate → HCID 59425956, compound

HRID 506066Notes

Reaction equation

HRID 506066 reaction equation
[NH2:1][CH2:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[N:12]([CH2:24][CH3:25])[C:13]3[C:18]([C:19]=2[C:20]#[N:21])=[CH:17][CH:16]=[C:15]([O:22][CH3:23])[CH:14]=3)=[CH:7][CH:6]=1.[CH2:26]([N:28]=[C:29]=[O:30])[CH3:27]>N1C=CC=CC=1>[C:20]([C:19]1[C:18]2[C:13](=[CH:14][C:15]([O:22][CH3:23])=[CH:16][CH:17]=2)[N:12]([CH2:24][CH3:25])[C:11]=1[C:8]1[CH:9]=[CH:10][C:5]([O:4][CH2:3][CH2:2][NH:1][C:29]([NH:28][CH2:26][CH3:27])=[O:30])=[CH:6][CH:7]=1)#[N:21]

Participants

4

Reactant 2

HCID 8022Ethyl isocyanateHCID 59425830HCID 59425830, compound

Product 1

HCID 59425956HCID 59425956, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

2-[4-(2-Aminoethoxy)phenyl]-1-ethyl-6-methoxy-1H-indole-3-carbonitrile (30 mg, 0.09 mmol), prepared as in example 1BB, is combined with ethyl isocyanate (18 μL, 0.21 mmol) and pyridine (300 μL). This mixture is stirred at room temperature for 90 minutes, and is then partitioned between EtOAc and aqueous HCl. The organic layer is dried and concentrated. Purification by silica gel chromatography (EtOAc) yields 1-{2-[4-(3-cyano-1-ethyl-6-methoxy-1H-indol-2-yl)-phenoxy]-ethyl}-3-ethyl-urea (34 mg, 93%) as a white solid.

Workup

  1. customis then partitioned between EtOAc and aqueous HCl
  2. customThe organic layer is dried
  3. concentrationconcentrated
  4. customPurification by silica gel chromatography (EtOAc)

Sources & evidence

ORD record
ord-8388abd0590c497097fb3384c43de56d
Source dataset
uspto-grants-2010_08
Patent number
US07781478B2

Reaction notes

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