Hydrochloric Acid → HCID 67314888, compound
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+].[CH2:22]([CH:24]1[O:28][C:27](=O)[C:26]2[S:30][CH:31]=[CH:32][C:25]1=2)[CH3:23].Cl>C1COCC1>[CH2:22]([CH:24]1[O:28][C:27](=[C:5]2[C:4]3[C:8](=[CH:9][CH:10]=[C:2]([F:1])[CH:3]=3)[NH:7][C:6]2=[O:11])[C:26]2[S:30][CH:31]=[CH:32][C:25]1=2)[CH3:23]Participants
Conditions
- Temperature
- 0 °C
Procedure
A solution of 5-fluoro-1,3-dihydro-indol-2-one (91 mg, 0.6 mmol.) in THF (1 mL) is cooled to 0° C. under an Argon atmosphere and treated with a solution of lithium bis(trimethylsilyl)amide (1.2 mL of a 1 M solution in THF, 1.2 mmol) dropwise. The resulting solution is stirred at 0° C. for 10 min and warmed to room temperature. A solution of 4-ethyl-4H-thieno[2,3-c]furan-6-one, (67 mg, 0.4 mmol) in THF (1.5 mL) 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 (50 mL). 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 to give the title compound as a yellow solid (68mg, 57%).
Workup
- temperaturewarmed to 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
Sources & evidence
- ORD record
- ord-3e0005307e644b5b992a1a2e7f8f6d0a
- Source dataset
- uspto-grants-2011_07
- Patent number
- US07977351B2
Reaction notes
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