Phenyl chloroformate → Phenyl [5-cyano-3-(2-ethoxyphenyl)-2-oxo-2,3-dihydro-1H-indol-3-yl]-carbamate

HRID 219758Notes

Reaction equation

HRID 219758 reaction equation
Cl[C:2]([O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:3].[NH2:11][C:12]1([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[O:30][CH2:31][CH3:32])[C:20]2[C:15](=[CH:16][CH:17]=[C:18]([C:21]#[N:22])[CH:19]=2)[NH:14][C:13]1=[O:23]>N1C=CC=CC=1>[C:21]([C:18]1[CH:19]=[C:20]2[C:15](=[CH:16][CH:17]=1)[NH:14][C:13](=[O:23])[C:12]2([NH:11][C:2](=[O:3])[O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[O:30][CH2:31][CH3:32])#[N:22]

Participants

4

Reactant 2

HCID 15891Phenyl chloroformateHCID 665930703-Amino-5-cyano-3-(2-ethoxyphenyl)indol-2-one

Product 1

HCID 86633613Phenyl [5-cyano-3-(2-ethoxyphenyl)-2-oxo-2,3-dihydro-1H-indol-3-yl]-carbamateYield 111%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

1.2 ml (9.38 mMol) of phenyl chloroformate were added dropwise to 2.5 g (8.5 mMol) of product 2a dissolved in 50 ml of pyridine at 0° C. The reaction solution was then stirred at room temperature for 16 h. The solution was subsequently poured into ice-water, and the aqueous phase was extracted with ethyl acetate (AcOEt). The organic phase was washed several times with water, dried and concentrated in vacuo. 3.9 g of the product were obtained.

Workup

  1. extractionthe aqueous phase was extracted with ethyl acetate (AcOEt)
  2. washThe organic phase was washed several times with water
  3. customdried
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f0266f4f4a8441b9928daa38ea398f21
Source dataset
uspto-grants-2012_06
Patent number
US08202870B2

Reaction notes

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