Hydrochloric Acid → HCID 67315275, 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[C:32]2[C:27](=[N:28][CH:29]=[CH:30][CH:31]=2)[C:26](=O)[O:25]1)[CH3:23].Cl>C1COCC1>[CH2:22]([CH:24]1[C:32]2[C:27](=[N:28][CH:29]=[CH:30][CH:31]=2)[C:26](=[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])[O:25]1)[CH3:23]Participants
Conditions
- Temperature
- 0 °C
Procedure
A solution of 5-fluoro-1,3-dihydro-indol-2-one (966 mg, 6.4 mmol.) in THF (6 mL) is cooled to 0° C. under an Argon atmosphere and treated with a solution of lithium bis(trimethylsilyl)amide (12.8 mL of a 1 M solution in THF, 12.8 mmol) dropwise. The resulting solution is stirred at 0° C. for 10 min and warmed to room temperature. A solution of 5-ethyl-5H-furo[3,4-b]pyridin-7-one, (697 mg, 4.27 mmol) in THF (7 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 (160 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 washed with small volumes of ethyl acetate (10×3 mL) and dried to give the title compound as a yellow solid (205 mg, 16%).
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
- washwashed with small volumes of ethyl acetate (10×3 mL)
- customdried
Sources & evidence
- ORD record
- ord-29dd0aaf17dd4725b77567ca1df4f9e0
- Source dataset
- uspto-grants-2011_07
- Patent number
- US07977351B2
Reaction notes
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