Hydrochloric Acid → HCID 76798883, compound

HRID 1011386Notes

Reaction equation

HRID 1011386 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[C:28]2[CH2:29][O:30][C:31](=O)[C:27]=2[CH:26]=[CH:25][N:24]=1.Cl>C1COCC1>[Cl:22][C:23]1[C:28]2[CH2:29][O:30][C:31](=[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])[C:27]=2[CH:26]=[CH:25][N:24]=1

Participants

6

Procedure

A solution of 5-fluoro-1,3-dihydro-indol-2-one (825 mg, 5.46 mmol.) in THF (5 mL) is cooled to 0° C. under an Argon atmosphere and treated with a solution of lithium bis(trimethylsilyl)amide (11 mL of a 1 M solution in THF, 11 mmol) dropwise. The resulting solution is stirred at room temperature for 10 min. A solution of 4-chloro-3H-furo[3,4-c]pyridin-1-one (620 mg, 3.67 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 then 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 (810 mg, 73%).

Workup

  1. stirringThe resulting solution is stirred for 4 h
  2. temperatureThe resulting mixture is heated to 90° C. for 2 h
  3. stirringstirred at room temperature for 36 h
  4. customThe precipitate which formed
  5. filtrationis collected by filtration
  6. washwashed with small volumes of ethyl acetate (10×3 mL)
  7. customdried under vacuum

Sources & evidence

ORD record
ord-567bbe87073549959709575d570fa31b
Source dataset
uspto-grants-2011_07
Patent number
US07977351B2

Reaction notes

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