Ethyl bromoacetate → (6-Chloro-3-methanesulfonyl-indol-1-yl)-acetic acid ethyl ester

HRID 23384Notes

Reaction equation

[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([S:11]([CH3:14])(=[O:13])=[O:12])=[CH:7][NH:8]2)=[CH:4][CH:3]=1.[H-].[Na+].Br[CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20]>CN1CCCC1=O>[CH2:22]([O:21][C:19](=[O:20])[CH2:18][N:8]1[C:9]2[C:5](=[CH:4][CH:3]=[C:2]([Cl:1])[CH:10]=2)[C:6]([S:11]([CH3:14])(=[O:13])=[O:12])=[CH:7]1)[CH3:23]

Participants

Conditions

Temperature: 0 °C

Procedure

6-Chloro-3-methanesulfonyl-1H-indole (1.35 g, 5.88 mmole) was dissolved in anhydrous N-methylpyrrolidin-2-one (15 ml), cooled to 0° C. and placed under a nitrogen atmosphere. Sodium hydride (60% in oil, 0.28 g, 7 mmole) was added all at once and the mixture was stirred until the evolution of gas ceased (ca. 20-30 minutes). Ethyl bromoacetate (1.08 g, 6.47 mmole) was added all at once and the mixture was stirred for 30 minutes. The reaction mixture was partitioned between ethyl acetate and water, the organic layer was washed three times with water, dried over magnesium sulfate, filtered, and evaporated to dryness. The crude material thus obtained was purified by chromatography on silica gel, eluting with ethyl acetate-hexane (1:9) to (4:6) to afford 1.463 g of (6-chloro-3-methanesulfonyl-indol-1-yl)-acetic acid ethyl ester.

Workup

custom(ca. 20-30 minutes)
stirringwas stirred for 30 minutes
customThe reaction mixture was partitioned between ethyl acetate and water
washthe organic layer was washed three times with water
dry with materialdried over magnesium sulfate
filtrationfiltered
customevaporated to dryness
customThe crude material thus obtained
customwas purified by chromatography on silica gel
washeluting with ethyl acetate-hexane (1:9) to (4:6)

Sources & evidence

ORD record: ord-a7f9cf999999406c94a48cfc03fc066f
Source dataset: uspto-grants-2005_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06852726B2

Reaction notes

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