Ethyl Acetate → N-(1-Octyl-5-hydroxymethyl-4,6-dimethylindolin-7-yl)-2,2-dimethylpropanamide

HRID 1107942Notes

Reaction equation

[OH:1][CH2:2][C:3]1[C:4]([CH3:20])=[C:5]2[C:9](=[C:10]([NH:13][C:14](=[O:19])[C:15]([CH3:18])([CH3:17])[CH3:16])[C:11]=1[CH3:12])[NH:8][CH2:7][CH2:6]2.I[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29].C([O-])([O-])=O.[K+].[K+].CCOC(C)=O>CN(C=O)C>[CH2:22]([N:8]1[C:9]2[C:5](=[C:4]([CH3:20])[C:3]([CH2:2][OH:1])=[C:11]([CH3:12])[C:10]=2[NH:13][C:14](=[O:19])[C:15]([CH3:16])([CH3:17])[CH3:18])[CH2:6][CH2:7]1)[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29]

Participants

Conditions

Temperature: 50 °C

Procedure

N-(5-Hydroxymethyl-4,6-dimethylindolin-7-yl)-2,2-dimethylpropanamide (1.5 g) was dissolved in DMF (15 ml) and 1-iodooctane (2.6 g) and K2CO3 (1.5 g) were added, which was followed by stirring under a nitrogen atmosphere at 50° C. for 2 hr. AcOEt (200 ml) was added, and the mixture was washed with water and dried over anhydrous sodium sulfate. AcOEt was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: CHCl3 /MeOH=1/0-10/1) to give 1.0 g of the title compound.

Workup

washthe mixture was washed with water
dry with materialdried over anhydrous sodium sulfate
customAcOEt was 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-1582324bac03432dbb175cf8c51217a1
Source dataset: uspto-grants-2000_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06063806

Reaction notes

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