Sodium ethoxide → HCID 59003298, compound

HRID 2267568Notes

Reaction equation

HRID 2267568 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].[CH3:30][CH2:31][O-:32].[Na+]>C(O)C>[CH2:31]([O:32][CH2:2][CH2:1][S:3]([N:6]1[CH2:7][CH2:8][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)[CH2:10][CH2:11]1)(=[O:5])=[O:4])[CH3:30]

Participants

4

Reactant 2

HCID 2723922Sodium ethoxideHCID 59003347HCID 59003347, compound

Product 1

HCID 59003298HCID 59003298, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

The mixture of 3-[1-(ethenylsulfonyl)-4-piperidinyl]-5-phenyl-1H-indole-7-carboxamide (23 mg, 0.056 mmol), NaOEt (10 mg) in ethanol (1 mL) was refluxed at 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 (15.0 mg, 59%).

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-e49c5e8237844f46a92da262bdb997fe
Source dataset
uspto-grants-2010_12
Patent number
US07858796B2

Reaction notes

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