Hydrochloric Acid → HCID 76798892, 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+].[Cl:22][C:23]1[N:28]=[CH:27][C:26]2[C:29](=O)[O:30][CH:31]([CH2:32][CH2:33][CH3:34])[C:25]=2[C:24]=1[Cl:36].Cl>C1COCC1>[Cl:22][C:23]1[N:28]=[CH:27][C:26]2[C:29](=[C:5]3[C:4]4[C:8](=[CH:9][CH:10]=[C:2]([F:1])[CH:3]=4)[NH:7][C:6]3=[O:11])[O:30][CH:31]([CH2:32][CH2:33][CH3:34])[C:25]=2[C:24]=1[Cl:36]Participants
Conditions
- Temperature
- 0 °C
Procedure
A solution of 5-fluoro-1,3-dihydro-indol-2-one (2.88 g, 19.1 mmol.) in THF (20 mL) is cooled to 0° C. under an argon atmosphere and treated with a solution of lithium bis(trimethylsilyl)amide (38 mL of a 1 M solution in THF, 38.0 mmol) dropwise. The resulting solution is stirred at 0° C. for 10 min and warmed room temperature. A solution of 6,7-dichloro-1-propyl-1H-furo[3,4-c]pyridin-3-one, (3.13 g, 12.72 mmol) in THF (20 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 (350 mL). The resulting mixture is heated to 90° C. for 2 h and then stirred at room temperature for 36 h. The precipitate which formed is collected by filtration and washed with small volumes of ethyl acetate (10×3 mL) to give the title compound as a yellow solid (1.75 g, 36%).
Workup
- temperaturewarmed room temperature
- 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)
Sources & evidence
- ORD record
- ord-88d79e020cb74561a7da7bdb0d13574a
- Source dataset
- uspto-grants-2011_07
- Patent number
- US07977351B2
Reaction notes
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