Phenyl chloroformate → 5-Cyano-1-(2,4-dimethoxybenzenesulfonyl)-3-(2-ethoxyphenyl)-2-oxo-2,3-dihydro-1-H-indol-3-yl phenyl carbonate

HRID 1091548Notes

Reaction equation

HRID 1091548 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([S:12]([C:15]1[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][C:16]=1[O:23][CH3:24])(=[O:14])=[O:13])[C:7](=[O:25])[C:6]2([OH:35])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[O:32][CH2:33][CH3:34])#[N:2].Cl[C:37]([O:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)=[O:38]>N1C=CC=CC=1.C(Cl)Cl>[C:37](=[O:38])([O:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)[O:35][C:6]1([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=2[O:32][CH2:33][CH3:34])[C:5]2[C:9](=[CH:10][CH:11]=[C:3]([C:1]#[N:2])[CH:4]=2)[N:8]([S:12]([C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][C:16]=2[O:23][CH3:24])(=[O:14])=[O:13])[C:7]1=[O:25]

Participants

5

Reactant 2

HCID 15891Phenyl chloroformateHCID 665929935-Cyano-1-(2,4-dimethoxybenzenesulfonyl)-3-hydroxy-3-(2-ethoxyphenyl)-indol-2-one

Product 1

HCID 866328045-Cyano-1-(2,4-dimethoxybenzenesulfonyl)-3-(2-ethoxyphenyl)-2-oxo-2,3-dihydro-1-H-indol-3-yl phenyl carbonateYield 65.1%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

1.5 g (3.0 mmol) of the product 1c were dissolved in 30 ml of pyridine. At 0° C., 1.7 g (10.6 mmol) of phenyl chloroformate were rapidly added dropwise. This reaction solution was stirred for 60 minutes before being stirred into ice-water. The resulting precipitate was isolated, dissolved in methylene chloride, dried and concentrated in vacuo. The resulting residue was crystallized with Et2O/n-pentane. 1.2 g of the intermediate were obtained.

Workup

  1. customThe resulting precipitate was isolated
  2. customdried
  3. concentrationconcentrated in vacuo
  4. customThe resulting residue was crystallized with Et2O/n-pentane

Sources & evidence

ORD record
ord-f06af42dbc57412e98e1e2a7cf4a1703
Source dataset
uspto-grants-2012_03
Patent number
US08129389B2

Reaction notes

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