Potassium Iodide → HCID 67615848, compound

HRID 1468059Notes

Reaction equation

Cl[CH2:2][C:3]([N:5]1[CH2:10][CH2:9][CH:8]([O:11][C:12]2[CH:13]=[N:14][C:15]([N:18]3[C:26]4[C:21](=[CH:22][C:23]([S:27]([CH3:30])(=[O:29])=[O:28])=[CH:24][CH:25]=4)[CH:20]=[CH:19]3)=[CH:16][CH:17]=2)[CH2:7][CH2:6]1)=[O:4].[I-].[K+].[NH:33]1[CH2:37][CH2:36][CH2:35][CH2:34]1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH3:30][S:27]([C:23]1[CH:22]=[C:21]2[C:26](=[CH:25][CH:24]=1)[N:18]([C:15]1[N:14]=[CH:13][C:12]([O:11][CH:8]3[CH2:9][CH2:10][N:5]([C:3](=[O:4])[CH2:2][N:33]4[CH2:37][CH2:36][CH2:35][CH2:34]4)[CH2:6][CH2:7]3)=[CH:17][CH:16]=1)[CH:19]=[CH:20]2)(=[O:28])=[O:29]

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 2-chloro-1-(4-((6-(5-(methylsulfonyl)-1H-indol-1-yl)pyridin-3-yl)oxy)piperidin-1-yl)ethanone (0.080 g, 0.179 mmol) in DMF (2 mL), potassium iodide (0.009 g, 0.054 mmol), pyrrolidine (0.044 mL, 0.536 mmol), potassium carbonate (0.025 g, 0.179 mmol) were added and stirred at 80° C. for 45 minutes. The reaction was quenched by adding water (20 mL), the mixture was extracted with ethyl acetate, organic layer was concentrated under reduced pressure. The resulting crude was purified by flash column chromatography to give 1-(4-((6-(5-(methylsulfonyl)-1H-indol-1-yl)pyridin-3-yl)oxy)piperidin-1-yl)-2-(pyrrolidin-1-yl)ethanon (0.045 g, 52.32%).

Workup

customThe reaction was quenched
additionby adding water (20 mL)
extractionthe mixture was extracted with ethyl acetate, organic layer
concentrationwas concentrated under reduced pressure
customThe resulting crude was purified by flash column chromatography

Sources & evidence

ORD record: ord-7f8ebdf8183946828fd37084747e55f7
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09000175B2

Reaction notes

Loading…