Ethyl Acetate → Ethyl 5-fluoro-1-(3-fluorobenzyl)-1H-indole-2-carboxylate

HRID 2217146Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:5]2.[F:16][C:17]1[CH:18]=[C:19]([CH:22]=[CH:23][CH:24]=1)[CH2:20]Cl.C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>CN(C)C=O>[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:20][C:19]1[CH:22]=[CH:23][CH:24]=[C:17]([F:16])[CH:18]=1)[C:6]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:5]2

Participants

Conditions

Temperature: 60 °C

Procedure

A suspension of 0.207 g (1 mmol) of ethyl 5-fluoro-1H-indole-2-carboxylate, 0.173 g (1.2 mmol) of 3-fluorobenzyl chloride and 0.276 g (2 mmol) of potassium carbonate in 10 ml of dimethylformamide is stirred for 24 hours at 60° C. The reaction mixture is then cooled and poured into a mixture of ice-water and ethyl acetate. After allowing the phases to separate by settling, the organic phase is separated out and then washed with twice 50 ml of water and then with 50 ml of saturated sodium chloride solution. The solution is dried over magnesium sulfate and filtered, and the filtrate is then concentrated under reduced pressure. 0.195 g of an oil is obtained, which is used without further purification in the following step.

Workup

temperatureThe reaction mixture is then cooled
customto separate
customthe organic phase is separated out
washwashed with twice 50 ml of water
dry with materialThe solution is dried over magnesium sulfate
filtrationfiltered
concentrationthe filtrate is then concentrated under reduced pressure

Sources & evidence

ORD record: ord-79f34d1c7e2440ac821cb13010068d08
Source dataset: uspto-grants-2008_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07407950B2

Reaction notes

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