Sodium hydride → HCID 58974987, compound

HRID 737051Notes

Reaction equation

HRID 737051 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([C:10](=[O:18])[CH2:11][N:12]2[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]2)=[CH:2]1.[H-].[Na+].[F:21][C:22]1[CH:41]=[CH:40][C:25]([CH2:26][NH:27][C:28]([C:30]2[CH:35]=[CH:34][C:33]([S:36](Cl)(=[O:38])=[O:37])=[CH:32][CH:31]=2)=[O:29])=[CH:24][CH:23]=1>CN(C=O)C>[F:21][C:22]1[CH:23]=[CH:24][C:25]([CH2:26][NH:27][C:28](=[O:29])[C:30]2[CH:35]=[CH:34][C:33]([S:36]([N:1]3[C:9]4[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=4)[C:3]([C:10](=[O:18])[CH2:11][N:12]4[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]4)=[CH:2]3)(=[O:37])=[O:38])=[CH:32][CH:31]=2)=[CH:40][CH:41]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 34864Ketone, 3-indolyl piperidinomethylHCID 589751254-(4-Fluoro-benzylcarbamoyl)-benzenesulfonyl chloride

Product 1

HCID 58974987HCID 58974987, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

Slowly add 1-(1H-Indol-3-yl)-2-piperidin-1-yl-ethanone (199 mg, 0.821 mmol, 1.0 eq) as a 2 ml DMF solution to a flask under N2 containing sodium hydride (36 mg, 60 wt % on oil, 0.903 mmol, 1.1 eq) in 2 ml DMF solution. Stir solution for 5 minutes. Slowly add 4-(4-Fluoro-benzylcarbamoyl)-benzenesulfonyl chloride (296 mg, 0.903 mmol, 1.1 eq) as a 3 ml DMF solution. Stir reaction for 18 hours at room temperature. Strip reaction of solvent and purify on silica gel chromatography to give N-(4-Fluoro-benzyl)-4-[3-(2-piperidin-1-yl-acetyl)-indole-1-sulfonyl]-benzamide (249 mg, 57% yield). Mass Spectrum (m/e): 534 (MH+).

Workup

  1. customreaction for 18 hours at room temperature
  2. customStrip reaction of solvent
  3. custompurify on silica gel chromatography

Sources & evidence

ORD record
ord-a61c163ce6754524869ec62312a00324
Source dataset
uspto-grants-2009_09
Patent number
US07595339B2

Reaction notes

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