Hydrochloric Acid → HCID 67314844, 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:28]2[CH:29]=[N:30][CH:31]=[CH:32][C:27]=2[C:26](=O)[O:25]1)[CH3:23].Cl>C1COCC1>[CH2:22]([CH:24]1[C:28]2[CH:29]=[N:30][CH:31]=[CH:32][C:27]=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
Procedure
A solution of 5-fluoro-1,3-dihydro-indol-2-one (936 mg, 6.20 mmol.) in THF (6 mL) is cooled to 0° C. under an argon atmosphere and treated with a solution of lithium bis(trimethylsilyl)amide (12.4 mL of a 1 M solution in THF, 12.4 mmol) dropwise. The resulting solution is stirred at room temperature for 10 min. A solution of 3-ethyl-3H-furo[3,4-c]pyridin-1-one (674 mg, 4.13 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 2 h 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 under vacuum to give the title compound as a yellow solid (720 mg, 59%).
Workup
- stirringThe resulting solution is stirred for 4 h
- temperatureThe resulting mixture is heated to 90° C. for 2 h
- 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 under vacuum
Sources & evidence
- ORD record
- ord-e1d582ab5cc84540b35e8df3b441cb85
- Source dataset
- uspto-grants-2011_07
- Patent number
- US07977351B2
Reaction notes
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