Indole → HCID 25030896, compound

HRID 1163073Notes

Reaction equation

HRID 1163073 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[H-].[Na+].Cl.Cl[CH2:14][C:15]1[CH:30]=[CH:29][C:18]([C:19]([N:21]2[CH2:25][CH2:24][CH:23]([N:26]([CH3:28])[CH3:27])[CH2:22]2)=[O:20])=[CH:17][CH:16]=1>CN(C=O)C>[N:1]1([CH2:14][C:15]2[CH:16]=[CH:17][C:18]([C:19]([N:21]3[CH2:25][CH2:24][CH:23]([N:26]([CH3:27])[CH3:28])[CH2:22]3)=[O:20])=[CH:29][CH:30]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1

Participants

5

Reactant 3

HCID 798IndoleHCID 24758Sodium hydrideHCID 68425818HCID 68425818, compound

Product 1

HCID 25030896HCID 25030896, compoundYield 72.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of indole (29 mg, 0.25 mmol) in DMF (5 mL) at room temperature is treated with sodium hydride (30 mg), stirred for 10 minutes, treated with 1-(4-chloromethylbenzoyl)-3-(N,N-dimethylamino)pyrrolidine hydrochloride (113 mg, 0.37 mmol) stirred at room temperature overnight and concentrated in vacuo. The resultant residue is dissolved in a mixture of DMSO, MeOH and water (1.5 mL) and purified by reverse-phase semi-preparative HPLC to give the title product as a white powder (63 mg), identified by HPLC and mass spectral analyses. MS [348.2 m/e (M+H)], retention time 2.58 min.

Workup

  1. stirringstirred at room temperature overnight
  2. concentrationconcentrated in vacuo
  3. dissolutionThe resultant residue is dissolved in a mixture of DMSO, MeOH and water (1.5 mL)
  4. custompurified by reverse-phase semi-preparative HPLC

Sources & evidence

ORD record
ord-e8dd89e8ef2a4555b9944f6296fbf919
Source dataset
uspto-grants-2010_10
Patent number
US07820825B2

Reaction notes

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