Sodium Iodide → HCID 59003315, compound

HRID 2267570Notes

Reaction equation

HRID 2267570 reaction equation
[CH:1]([S:3]([N:6]1[CH2:11][CH2:10][CH:9]([C:12]2[C:20]3[C:15](=[C:16]([C:27]([NH2:29])=[O:28])[CH:17]=[C:18]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)[CH:19]=3)[NH:14][CH:13]=2)[CH2:8][CH2:7]1)(=[O:5])=[O:4])=[CH2:2].[N:30]1([CH2:36][CH2:37][OH:38])[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]1.C([O-])([O-])=O.[K+].[K+].[I-].[Na+]>CS(C)=O>[C:21]1([C:18]2[CH:19]=[C:20]3[C:15](=[C:16]([C:27]([NH2:29])=[O:28])[CH:17]=2)[NH:14][CH:13]=[C:12]3[CH:9]2[CH2:8][CH2:7][N:6]([S:3]([CH2:1][CH2:2][O:38][CH2:37][CH2:36][N:30]3[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]3)(=[O:5])=[O:4])[CH2:11][CH2:10]2)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 18232N-PiperidinoethanolHCID 59003347HCID 59003347, compound

Product 1

HCID 59003315HCID 59003315, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
80 °C

Procedure

The mixture of 3-[1-(ethenylsulfonyl)-4-piperidinyl]-5-phenyl-1H-indole-7-carboxamide (21 mg, 0.05 mmol) in DMSO (1.0 mL), were added 2-(1-piperidinyl)ethanol (64.6 mg, 0.5 mmol), K2CO3 (35.0 mg, 0.35 mmol) and sodium iodide (0.5 mg). The reaction solution was heated to 80° C. overnight. The reaction mixture was concentrated and purified by reverse phase HPLC (water/CH3CN, 0.1% TFA 10-90%) to give the title compound (12.0 mg, 50%).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. custompurified by reverse phase HPLC (water/CH3CN, 0.1% TFA 10-90%)

Sources & evidence

ORD record
ord-c54e15275d6b4a908d71ec24c7cb9762
Source dataset
uspto-grants-2010_12
Patent number
US07858796B2

Reaction notes

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