Sodium Chloride → N-[2-(1-acetyl-6-chloro-5-methoxyindolin-3-yl)ethyl]acetamide

HRID 612529Notes

Reaction equation

HRID 612529 reaction equation
[C:1]([N:4]1[C:12]2[C:7](=[CH:8][C:9]([O:13][CH3:14])=[CH:10][CH:11]=2)[CH:6]([CH2:15][CH2:16][NH:17][C:18](=[O:20])[CH3:19])[CH2:5]1)(=[O:3])[CH3:2].[Cl-:21].[Na+]>C(#N)C.ClCCl>[C:1]([N:4]1[C:12]2[C:7](=[CH:8][C:9]([O:13][CH3:14])=[C:10]([Cl:21])[CH:11]=2)[CH:6]([CH2:15][CH2:16][NH:17][C:18](=[O:20])[CH3:19])[CH2:5]1)(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 5234Sodium ChlorideHCID 23283701N-[2-(1-acetyl-5-methoxyindolin-3-yl)ethyl]acetamide

Product 1

HCID 23283706N-[2-(1-acetyl-6-chloro-5-methoxyindolin-3-yl)ethyl]acetamide

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of N-[2-(1-acetyl-5-methoxyindolin-3-yl)ethyl]acetamide (0.29 mmol) in acetonitrile (1.5 ml) is added bis(trifluoroacetoxyiodobenzene) (PIFA 1.2 eq) and the medium is left stirring for 1 min at room temperature. Saturated sodium chloride solution (0.5 ml) is next added and, after 15 min, the mixture is diluted with dichloromethane (10 ml) and dried over magnesium sulphate. The crude product obtained after evaporation is chromatographed on a column of flash silica (5/95 methanol/dichloromethane) and N-[2-(l-acetyl-6-chloro-5-methoxyindolin-3-yl)ethyl]acetamide (70 mg) is thus obtained.

Workup

  1. waitthe medium is left
  2. dry with materialdried over magnesium sulphate

Sources & evidence

ORD record
ord-7f9f2a6716c848deb5b5d78d181730e6
Source dataset
uspto-grants-1999_12
Patent number
US06004991

Reaction notes

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