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Sodium Methoxide → 5-bromo-3-(1-{[2-(methyloxy)ethyl]sulfonyl}-4-piperidinyl)-1H-indole-7-carboxamide

HRID 2267506
Notes
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Reaction equation

HRID 2267506 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]([CH:23]=[CH2:24])(=[O:22])=[O:21])[CH2:16][CH2:15]1.[CH3:25][O-:26].[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][O:26][CH3:25])(=[O:22])=[O:21])[CH2:16][CH2:15]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 590033355-bromo-3-[1-(ethenylsulfonyl)-4-piperidinyl]-1H-indole-7-carboxamide

Product 1

HCID 596006625-bromo-3-(1-{[2-(methyloxy)ethyl]sulfonyl}-4-piperidinyl)-1H-indole-7-carboxamideYield 63%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
80 °C

Procedure

The mixture of 5-bromo-3-[1-(ethenylsulfonyl)-4-piperidinyl]-1H-indole-7-carboxamide (150 mg, 0.36 mmol), sodium methoxide in methanol (25%, 1.0 mL) and methanol (2.0 mL) was stirred at 80° C. for 1 hr. After which time the reaction mixture was concentrated under reduced pressure. The residue was purified by combiflash to give the title compound (100.0 mg, 63%).

Workup

  1. concentrationAfter which time the reaction mixture was concentrated under reduced pressure
  2. customThe residue was purified by combiflash

Sources & evidence

ORD record
ord-a0ca8dd793324aeaa6185e7329f6c398
Source dataset
uspto-grants-2010_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07858796B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes