Potassium Iodide → HCID 89740097, compound

HRID 2206556Notes

Reaction equation

HRID 2206556 reaction equation
[CH3:1][C:2]1[NH:3][C:4]2[C:9]([C:10]=1[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])=[CH:8][CH:7]=[CH:6][CH:5]=2.Cl[CH:19]([CH3:23])[C:20](=[O:22])[CH3:21].C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>C(#N)C.O>[CH3:1][C:2]1[N:3]([CH:19]([C:20](=[O:22])[CH3:21])[CH3:23])[C:4]2[C:9]([C:10]=1[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])=[CH:8][CH:7]=[CH:6][CH:5]=2

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 200263-Chloro-2-butanoneHCID 80156864HCID 80156864, compound

Product 1

HCID 89740097HCID 89740097, compoundYield 23%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of tert-butyl 2-methyl-1H-indole-3-carboxylate (2 g, 8.65 mmol) and 3-chlorobutan-2-one (1.1 g, 10.38 mmol) in acetonitrile (18 mL) were added potassium carbonate (3.2 g, 25.8 mmol) and potassium iodide (1.4 g, 8.65 mmol). The reaction mixture was stirred at 90° C. overnight. To the reaction mixture was added water (20 mL). The aqueous layer was extracted with ethyl acetate (50 mL×4). The combined organic layers were dried over sodium sulfate and concentrated. The crude product was purified by silica gel column (petroleum ether/ethyl acetate 100:1 to 80:1) to give tert-butyl 2-methyl-1-(3-oxobutan-2-yl)-1H-indole-3-carboxylate (600 mg, yield: 23%) as a yellow oil. LRMS (M+H+) m/z: calcd 301.17. found 302.

Workup

  1. extractionThe aqueous layer was extracted with ethyl acetate (50 mL×4)
  2. dry with materialThe combined organic layers were dried over sodium sulfate
  3. concentrationconcentrated
  4. customThe crude product was purified by silica gel column (petroleum ether/ethyl acetate 100:1 to 80:1)

Sources & evidence

ORD record
ord-05626b3e499a4c2e861d63eeb8e83cbe
Source dataset
uspto-grants-2016_06
Patent number
US09371331B2

Reaction notes

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