Ethyl isocyanate → HCID 59425956, compound

HRID 907166Notes

Reaction equation

HRID 907166 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, was combined with ethyl isocyanate (18 μL, 0.21 mmol) and pyridine (300 μL). This mixture was stirred at room temperature for 90 minutes, and was then partitioned between EtOAc and aqueous HCl. The organic layer was dried and concentrated. Purification by silica gel chromatography (EtOAc) yielded 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. customwas then partitioned between EtOAc and aqueous HCl
  2. customThe organic layer was dried
  3. concentrationconcentrated
  4. customPurification by silica gel chromatography (EtOAc)

Sources & evidence

ORD record
ord-29f2e586b4a147378d6937842998e1b5
Source dataset
uspto-grants-2011_09
Patent number
US08013006B2

Reaction notes

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