Hydrochloric Acid → HCID 67313544, compound

HRID 1011418Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[CH2:5]2.C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[CH3:22][CH:23]1[O:27][C:26](=O)[C:25]2[S:29][CH:30]=[CH:31][C:24]1=2.Cl>C1COCC1>[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[C:5]2=[C:26]1[C:25]2[S:29][CH:30]=[CH:31][C:24]=2[CH:23]([CH3:22])[O:27]1

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of 5-fluoro-1,3-dihydro-indol-2-one in THF is cooled to 0° C. under an argon atmosphere and treated with a solution of lithium bis(trimethylsilyl)amide dropwise. The resulting solution is stirred at 0° C. for 10 min and warmed room temperature. A solution of 4-methyl-4H-thieno[2,3-c]furan-6-one (0.15 mmol), in THF is added dropwise to the reaction mixture. The resulting solution is stirred for 4 h. The reaction mixture is poured into aqueous 10% HCl solution. The resulting mixture is heated to 90° C. for 45 min and stirred at room temperature for 36 h. The precipitate which formed is collected by filtration and dried. The solid obtained is purified by chromatography (35% EtOAc-Hexanes) to give the title compound as a yellow solid (38 mg, 87%).

Workup

temperaturewarmed room temperature
stirringThe resulting solution is stirred for 4 h
temperatureThe resulting mixture is heated to 90° C. for 45 min
stirringstirred at room temperature for 36 h
customThe precipitate which formed
filtrationis collected by filtration
customdried
customThe solid obtained
customis purified by chromatography (35% EtOAc-Hexanes)

Sources & evidence

ORD record: ord-5aa8a971c8cb445db9e73283420185ed
Source dataset: uspto-grants-2011_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07977351B2

Reaction notes

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