Potassium Iodide → HCID 67807850, compound

HRID 1468062Notes

Reaction equation

HRID 1468062 reaction equation
Cl[CH2:2][C:3]([N:5]1[CH2:9][CH2:8][CH2:7][CH2:6]1)=[O:4].[I-].[K+].[CH3:12][S:13]([C:16]1[CH:17]=[C:18]2[C:22](=[CH:23][CH:24]=1)[N:21]([C:25]1[CH:30]=[CH:29][C:28]([O:31][CH:32]3[CH2:37][CH2:36][NH:35][CH2:34][CH2:33]3)=[CH:27][N:26]=1)[CH:20]=[CH:19]2)(=[O:15])=[O:14].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH3:12][S:13]([C:16]1[CH:17]=[C:18]2[C:22](=[CH:23][CH:24]=1)[N:21]([C:25]1[N:26]=[CH:27][C:28]([O:31][CH:32]3[CH2:37][CH2:36][N:35]([CH2:2][C:3]([N:5]4[CH2:9][CH2:8][CH2:7][CH2:6]4)=[O:4])[CH2:34][CH2:33]3)=[CH:29][CH:30]=1)[CH:20]=[CH:19]2)(=[O:14])=[O:15]

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 884401-(Chloroacetyl)pyrrolidine2×HCID 67616611HCID 67616611, compound

Product 1

HCID 67807850HCID 67807850, compoundYield 42.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a stirred solution of 2-chloro-1-(pyrrolidin-1-yl)ethanone (Intermediate 71) (0.055 g, 0.366 mmol) in DMF (2 mL), potassium iodide (0.023 g, 0.137 mmol), 5-(methylsulfonyl)-1-(5-(piperidin-4-yloxy)pyridin-2-yl)-1H-indole (0.170 g, 0.458 mmol) and potassium carbonate (0.064 g, 0.458 mmol) were added. The resulting mixture was heated at 80° C. for 45 minutes. Reaction was quenched with water and extracted with ethyl acetate. The organic extract was concentrated in vacuo and resultant residue was purified by column chromatography to yield title compound (0.075 g, 33.3%).

Workup

  1. customReaction
  2. customwas quenched with water
  3. extractionextracted with ethyl acetate
  4. extractionThe organic extract
  5. concentrationwas concentrated in vacuo and resultant residue
  6. customwas purified by column chromatography

Sources & evidence

ORD record
ord-db9e16dacdf64ac88ce372039c4b058f
Source dataset
uspto-grants-2015_04
Patent number
US09000175B2

Reaction notes

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