Sodium Methoxide → 5-bromo-3-(1-{[3-(methyloxy)propyl]sulfonyl}-4-piperidinyl)-1H-indole-7-carboxamide

HRID 2267503Notes

Reaction equation

HRID 2267503 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([C:11]([NH2:13])=[O:12])[CH:10]=1)[NH:7][CH:6]=[C:5]2[CH:14]1[CH2:19][CH2:18][N:17]([S:20]([CH2:23][CH2:24][CH2:25]Cl)(=[O:22])=[O:21])[CH2:16][CH2:15]1.[CH3:27][O-:28].[Na+]>CO>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([C:11]([NH2:13])=[O:12])[CH:10]=1)[NH:7][CH:6]=[C:5]2[CH:14]1[CH2:19][CH2:18][N:17]([S:20]([CH2:23][CH2:24][CH2:25][O:28][CH3:27])(=[O:22])=[O:21])[CH2:16][CH2:15]1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 590033105-bromo-3-{1-[(3-chloropropyl)sulfonyl]-4-piperidinyl}-1H-indole-7-carboxamide

Product 1

HCID 590033305-bromo-3-(1-{[3-(methyloxy)propyl]sulfonyl}-4-piperidinyl)-1H-indole-7-carboxamideYield 78%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The mixture of 5-bromo-3-{1-[(3-chloropropyl)sulfonyl]-4-piperidinyl}-1H-indole-7-carboxamide (23 mg, 0.050 mmol), 0.1 M NaOMe (1 ml) in methanol (1 mL) was refluxed overnight. The reaction mixture was concentrated and purified by reverse phase HPLC (water/CH3CN, 0.1% TFA 10-90%) to give the title compound (18.0 mg, 78%).

Workup

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

Sources & evidence

ORD record
ord-9ff8b67c688348baa15f64a9697dfe15
Source dataset
uspto-grants-2010_12
Patent number
US07858796B2

Reaction notes

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