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Sodium Iodide → HCID 16660201, compound

HRID 491039
Notes
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Reaction equation

HRID 491039 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][C:5]1[N:6]([C:14]2[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=2)[C:7]2[C:12]([CH:13]=1)=[CH:11][CH:10]=[CH:9][CH:8]=2.Cl[CH2:22][CH2:23][CH2:24][N:25]1[CH2:29][CH2:28][CH2:27][CH2:26]1.[H-].[Na+].[I-].[Na+]>CN(C)C=O>[CH3:1][O:2][CH2:3][CH2:4][C:5]1[N:6]([C:14]2[CH:15]=[CH:16][C:17]([O:20][CH2:22][CH2:23][CH2:24][N:25]3[CH2:29][CH2:28][CH2:27][CH2:26]3)=[CH:18][CH:19]=2)[C:7]2[C:12]([CH:13]=1)=[CH:11][CH:10]=[CH:9][CH:8]=2
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 24758Sodium hydrideHCID 113210281-(3-Chloropropyl)-pyrrolidineHCID 66593137HCID 66593137, compound

Product 1

HCID 16660201HCID 16660201, compoundYield 47.4%

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent

Conditions

Temperature
70 °C

Procedure

4-[2-(2-Methoxyethyl)indol-1-yl]phenol (0.39 mmol) was dissolved in N,N-dimethylformamide (4 mL), and 1-(3-chloropropyl)pyrrolidine (58 mg, 0.39 mmol), sodium hydride (19 mg, 60% dispersion in mineral oil, 0.47 mmol), and sodium iodide (59 mg, 0.39 mmol) were added. The reaction was heated at 70° C. for 1.5 hours, then carefully quenched with saturated sodium bicarbonate solution. The mixture was extracted with ethyl acetate, dried over MgSO4 and concentrated. The residue was purified by SiO2 chromatography to give 70 mg of the desired product. LC-MS (C24H30N2O2 calc'd 378) m/z 379 (M+H); 1H NMR (300 MHz, CDCl3) δ 7.60-7.56 (m, 1H), 7.25-7.21 (m, 2H), 7.10-7.00 (m, 5H), 6.45 (s, 1H), 4.11 (t, J=6.3 Hz, 2H), 3.57 (t, J=7.2 Hz, 2H), 3.30 (s, 3H), 2.89 (t, J=7.2 Hz, 2H), 2.74 (t, J=7.5 Hz, 2H), 2.65 (m, 4H), 2.16-2.05 (m, 2H), 1.90-1.81 (m, 4H).

Workup

  1. customcarefully quenched with saturated sodium bicarbonate solution
  2. extractionThe mixture was extracted with ethyl acetate
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. customThe residue was purified by SiO2 chromatography

Sources & evidence

ORD record
ord-8a1728154f214459a2e57bfb20f319a8
Source dataset
uspto-grants-2009_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07528262B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes