Ethyl Acetate → HCID 22632113, compound

HRID 1840433Notes

Reaction equation

[F:1][C:2]([F:13])([F:12])[S:3][C:4]1[N:5]=[CH:6][N:7]2[CH:11]=[CH:10][S:9][C:8]=12.[CH2:14]([Sn:18](Cl)([CH2:23][CH2:24][CH2:25][CH3:26])[CH2:19][CH2:20][CH2:21][CH3:22])[CH2:15][CH2:16][CH3:17].C[Si]([N-][Si](C)(C)C)(C)C.[Li+].C1COCC1.C(OCC)(=O)C>C1COCC1>[CH2:23]([Sn:18]([CH2:14][CH2:15][CH2:16][CH3:17])([CH2:19][CH2:20][CH2:21][CH3:22])[C:10]1[S:9][C:8]2=[C:4]([S:3][C:2]([F:1])([F:12])[F:13])[N:5]=[CH:6][N:7]2[CH:11]=1)[CH2:24][CH2:25][CH3:26]

Participants

Conditions

Temperature: -65 °C

Procedure

7-Trifluoromethylthioimidazo[5,1-b]thiazole (590 mg) was dissolved in 10 ml of THF under an argon atmosphere, and the solution was cooled to −65° C. Tri-n-butylstannyl chloride (2.07 ml) and 7.2 ml of a 1.0 N lithiumbis(trimethylsilyl)amide/THF solution were added dropwise in that order to the cooled solution. The temperature of the mixture was raised to −40° C. over a period of 30 min. Ethyl acetate (40 ml) was added to the reaction solution, and the mixture was washed with 40 ml of brine. The organic layer was dried over anhydrous magnesium sulfate, and was then filtered. The solvent was removed by distillation under the reduced pressure. The residue was purified by column chromatography on silica gel (hexane:ethyl acetate=4:1) to prepare 951 mg of the title compound.

Workup

temperatureThe temperature of the mixture was raised to −40° C. over a period of 30 min
washthe mixture was washed with 40 ml of brine
dry with materialThe organic layer was dried over anhydrous magnesium sulfate
filtrationwas then filtered
customThe solvent was removed by distillation under the reduced pressure
customThe residue was purified by column chromatography on silica gel (hexane:ethyl acetate=4:1)
customto prepare 951 mg of the title compound

Sources & evidence

ORD record: ord-7b424483ad81497793a840a131c21328
Source dataset: uspto-grants-2004_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06680313B2

Reaction notes

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