Potassium Acetate → N-(1-acetyl-5-acetoxymethyl-4,6-dimethylindolin-7-yl)-2,2-dimethylpropanamide

HRID 1531951Notes

Reaction equation

[C:1]([N:4]1[C:12]2[C:7](=[C:8]([CH3:23])[C:9]([CH2:21]Cl)=[C:10]([CH3:20])[C:11]=2[NH:13][C:14](=[O:19])[C:15]([CH3:18])([CH3:17])[CH3:16])[CH2:6][CH2:5]1)(=[O:3])[CH3:2].[C:24]([O-:27])(=[O:26])[CH3:25].[K+]>CC#N.CN(C=O)C>[C:1]([N:4]1[C:12]2[C:7](=[C:8]([CH3:23])[C:9]([CH2:21][O:27][C:24](=[O:26])[CH3:25])=[C:10]([CH3:20])[C:11]=2[NH:13][C:14](=[O:19])[C:15]([CH3:18])([CH3:17])[CH3:16])[CH2:6][CH2:5]1)(=[O:3])[CH3:2]

Participants

Conditions

Temperature: 60 °C

Procedure

N-(1-Acetyl-5-chloromethyl-4,6-dimethylindolin-7-yl)-2,2-dimethylpropanamide (7.0 g) was dissolved in a mixed solvent (50 ml) of CH3CN/DMF=1/1. Potassium acetate (12.0 g) was added and the mixture was stirred at 60° C. for 1 hr. CH3CN was evaporated under reduced pressure and AcOEt (200 ml) was added. After washing with water, the mixture was dried over anhydrous sodium sulfate, and AcOEt was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: CHCl3/MeOH=1/0−10/1) to give 7.5 g of N-(1-acetyl-5-acetoxymethyl-4,6-dimethylindolin-7-yl)-2,2-dimethylpropanamide.

Workup

customCH3CN was evaporated under reduced pressure and AcOEt (200 ml)
additionwas added
washAfter washing with water
dry with materialthe mixture was dried over anhydrous sodium sulfate, and AcOEt
customwas evaporated under reduced pressure
customThe residue was purified by silica gel column chromatography (eluent: CHCl3/MeOH=1/0−10/1)

Sources & evidence

ORD record: ord-adf04640066d49c387714a89db026c8d
Source dataset: uspto-grants-2001_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06200988B1

Reaction notes

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