Ethylene Glycol → 1-(4-Fluorobenzyl)-5-methanesulfonyl-2-(2-thiazolylmethyl)indole

HRID 1838374Notes

Reaction equation

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

Participants

Conditions

Temperature: 120 °C

Procedure

To a mixture of the compound obtained in Example 27 (6) (88 mg), potassium hydroxide (25 mg) and ethylene glycol (2.5 ml), hydrazine (65 mg) was added and the mixture was stirred at 120° C. for 3 hours. The reaction mixture was poured into water, extracted with chloroform, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The resulting residue was separated and purified twice with silica gel preparative thin-layer chromatography (hexane:ethyl acetate=1:1) and (chloroform:methanol=15:1) to obtain 39 mg of the desired product as a yellow oil.

Workup

additionwas added
extractionextracted with chloroform
dry with materialdried over anhydrous magnesium sulfate
concentrationconcentrated under reduced pressure
customThe resulting residue was separated
custompurified twice with silica gel preparative thin-layer chromatography (hexane:ethyl acetate=1:1) and (chloroform:methanol=15:1)

Sources & evidence

ORD record: ord-f83622680bbb4fc4b07694f57d2dec79
Source dataset: uspto-grants-2004_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06673797B1

Reaction notes

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